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Quality Control of [ 86357-14-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 86357-14-4 ]

SDS Specification

Alternatived Products of [ 86357-14-4 ]

Product Details of [ 86357-14-4 ]

CAS No. :	86357-14-4	MDL No. :	MFCD08457700
Formula :	C₁₅H₁₉N₅O₇	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PEZKHGVZZSQDPY-UHFFFAOYSA-N
M.W :	381.34	Pubchem ID :	135427290
Synonyms :	Triacetylganciclovir;Ganciclovir Triacetate	Chemical Name :	2-((2-Acetamido-6-oxo-1H-purin-9(6H)-yl)methoxy)propane-1,3-diyl diacetate

Safety of [ 86357-14-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 86357-14-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 86357-14-4 ]
Downstream synthetic route of [ 86357-14-4 ]

[ 86357-14-4 ] Synthesis Path-Upstream 1~1

1
[ 86357-14-4 ]
[ 88110-89-8 ]

Reference： [1] Patent: EP1837336, 2007, A1, . Location in patent: Page/Page column 10-11
[2] Patent: EP1837336, 2007, A1, . Location in patent: Page/Page column 11
[3] Patent: EP1837336, 2007, A1, . Location in patent: Page/Page column 11
[4] Patent: EP1837336, 2007, A1, . Location in patent: Page/Page column 11
[5] Patent: US2007/225305, 2007, A1, . Location in patent: Page/Page column 7
[6] Patent: US2007/225305, 2007, A1, . Location in patent: Page/Page column 7
[7] Patent: US2007/225305, 2007, A1, . Location in patent: Page/Page column 8
[8] Patent: US2007/225305, 2007, A1, . Location in patent: Page/Page column 7-8

[ 86357-14-4 ] Synthesis Path-Downstream 1~15

1
[ 86357-13-3 ]
[ 86357-14-4 ]

Reference： [1]Synthesis,1999,p. 625 - 628

Yield	Reaction Conditions	Operation in experiment
	Purification / work up;	Crude N2-acetyl-9- (1, 3-diacetoxy-2-propoxymethyl) guanine (100 kg) was added to the mixture of dichloromethane (500 lit) and methanol (40 lit). Temperature was raised to 30-35°C and maintained for 30 minutes and then activated carbon (5 kg) was added and stirred for another 30 minutes at the same temperature. Slowly cooled to 5°C and maintained for 30 minutes. Filtered through celite bed, removed the solvent completely by DISTILLATION, ADDED ACETONE (800 LIT. ) TO THE RESULTING MASS. COOLED TO 35°C, STIRRED FOR 60 minutes at 30-35°C. Filtered the solids and washed with acetone, yielding 80-82 kg of pure N2-ACETYL-9- (1, 3-diacetoxy-2-propoxymethyl) guanine.Data on chromatographic purity Before Purification After Purification N-9 isomer 95.08 98.90 DAG/MAG 2.77 0.1 N-7 isomer 0.62 0.11
	Purification / work up;	Crude N2-acetyl-9- (1, 3-diacetoxy-2-propoxymethyl) guanine (100 gm) was added to the mixture of dichloromethane (500 ml) and methanol (40 ml). Temperature was raised to 30-35°C and kept for 30 minutes, and then activated carbon (5 gm) was added and stirred for another 30 minutes at the same temperature. Slowly cooled to 8°C and maintained for 30 minutes. Filtered through celite bed and washed the bed using dichloromethane. Solvent was completely distilled off under vacuum. Charged fresh dichloromethane (200 ml) and heated up to 40°C followed by cooling to 2-5°C. Filtered the product and washed with dichloromethane. Collected the wet material and charged acetone (700 ml) to the wet mass and heated to reflux temperature. Cooled to 35°C stirred 60 minutes at 30-35°C. Filtered the solids and washed with acetone, yielding 68-72 gm of pure N2-acetyl-9- (1, 3-diacetoxy-2-propoxymethyl) guanine after drying. Data on chromatographic purity Before Purification After Purification N-9 isomer 88.73 98.63 DAG/MAG 7.9 0.31 N-7 isomer 1.08 0.25
	Purification / work up;	Crude N2-acetyl-9- (1, 3-diacetoxy-2-propoxymethyl) guanine (100 gm) was added TO THE DM WATER (250 ML. ) AT ROOM TEMPERATURE. TEMPERATURE WAS RAISED TO 70-75°C AND kept 30 minutes, all solids completely dissolved at the same temperature. Slowly cooled to room temperature followed by further cooling to 5-10°C and maintained for 60 minutes. Filtered the product at 5°C, yielding 58 gm of pure N2-ACETYL-9- (1, 3-diacetoxy-2- propoxymethyl) guanine after drying. Data on chromatographic purity Before Purification After Purification N-9 isomer 77.15 86.73 DAG/MAG 3.01 1.65 N-7 isomer 13.64 6.64

	Purification / work up;	Crude N2-ACETYL-9- (1, 3-diacetoxy-2-propoxymethyl) guanine (400 gm) was added TO METHANOL (1.25 LIT. ) AT ROOM TEMPERATURE. TEMPERATURE WAS RAISED TO 40-45°C AND KEPT for 30 minutes, all solids completely dissolved at the same temperature. Slowly cooled to room temperature followed by further cooling to 5°C and maintained for 60 minutes. Filtered the product at 5°C and washed using chilled methanol, yielding 220 gm of pure N2-ACETYL-9- (1, 3-DIACETOXY-2-PROPOXYMETHYL) guanine after drying. Data on chromatographic purity Before Purification After Purification N-9 isomer 88.41 94.09 DAG/MAG 1.71 0.34 N-7 isomer 4.83 1.06
		B. 2-Acetamido-9-(1,3-diacetoxy-2-propoxymethyl)hypoxanthine A mixture of 3.76 g (16 mmole) of diacetylguanine (VII), 4.96 g (20 mmole) of acetoxymethyl 1,3-diacetoxy-2-propyl ether (VI), 40 mg of ethanesulfonic acid, and 15 ml of triglyme in a flask fitted with a distillation adapter was heated under low vacuum in an oil bath at 155°-160°. The mixture gradually thinned enough to stir, and a clear distillate was slowly collected. The reaction mixture became a clear solution after about 75 minutes. After 3 hours the solution was cooled, and the product was induced to crystallize. After standing, the thick mixture was diluted with a small volume of 1,2-dimethoxyethane. The solid was collected on a filter and washed with small volumes of 1,2-dimethoxyethane followed by ethyl acetate to give 3.27 g of cream-colored crystals consisting of a mixture of 9- and 7-alkylated isomers as determined by TLC (9:1 CHCl3 --MeOH). (The 9-isomer runs more slowly than the 7-isomer in this system). The mother liquor provided an additional 0.65 g of material. The combined crops (3.92 g) were chromatographed twice on a silica gel column (elution with 97:3 and then 96:4 CH2 Cl2 --MeOH). Fractions containing nearly pure 9-alkylated isomer were combined and concentrated. Crystallization of the residues from a minimum amount of 1,2-dimethoxyethane yielded a first crop of 665 mg (white crystals, mp 171.5°-172.5°) and a second crop of 189 mg (mp 173°-173.5°). Both crops consisted of the pure 9-alkylated product as determined by TLC in comparison with an earlier batch fully characterized by NMR and elemental analysis.

Yield	Reaction Conditions	Operation in experiment
		A mixture of diacetyl guanine (100g, 0. 425MOLE), 2-acetoxymethoxy-1,3- diacetoxy propane (180g, 0.725 mole), P-TOLUENE SULFONIC acid monohydrate (5. 0G), N2-ACETYL-7- (1, 3-DIACETOXY-2-PROPOXYMETHYL) guanine (78g) in N, N- DIMETHYLFORMAMIDE (350ML) is heated at 95°C to 100°C under continuous stirring for 40 hours. After completion of the reaction, the solvents are removed under vacuum from the reaction mixture, yielding a dark brown syrup. The syrup is dissolved by heating in METHANOL (400M1). The solution is cooled to 0°C, stirred for 1 hour at 0 to 5°C. The crystalline product is filtered and washed with methanol (50ML) to YIELD N2-ACETYL-7- (1, 3-diacetoxy-2- propoxymethyl) guanine (54. 1G). Solvent is removed completely from the filtrate and METHANOL (100ML) and TOLUENE (800ML) were added to the residue and the mixture is heated to 60°C and then cooled to 5°C and stirred for 30 minutes. The crystalline product is filtered, washed with a mixture of methanol and toluene (1: 4), dried at 60-65°C to afford N2-ACETYL-9- (1, 3-DIACETOXY-2-PROPOXYMETHYL) guanine (114. OG).

4
diacetylguanine [ No CAS ]
[ 86357-13-3 ]
[ 86357-17-7 ]
[ 86357-14-4 ]

Yield	Reaction Conditions	Operation in experiment
46.7%	With phosphoric acid; In chloroform; N,N-dimethyl-formamide;	Example 7 Preparation of 9-[2-Acetoxy-1-(acetoxymethyl)ethoxy]methyl}-2-acetamidopurine-6-one (9) and 7-[2-acetoxy-1-(acetoxymethyl)ethoxy]methyl}-2-acetaminopurine-6-one (10) A mixture of diacetylguanine (10.575 g, 45 mmol), 2-acetoxymethoxy-1,3-diacetoxypropane (22.32 g, 90 mmol) and phosphoric acid (0.3 ml) in DMF (45 ml) was heated for three hours at 120° (oil bath 135°) with stirring. The suspension gradually became homogeneous. When TLC indicated the reaction was complete, the reaction solution was evaporated in vacuo to remove solvents yielding a dark-brown syrup. The syrup was dissolved in small amount of CHCl3 and applied to a column (silica gel 60, phi4*27 cm), eluted with CH3 OH:CHCl3 (0-3percent) to give 9 (8.0 g, 46.7percent) and 10 (5.1 g, 29.8percent). Compound 9: mp 165°-7° (ethyl acetate); Rf 0.49 (CH3 OH--CHCl3 =1:9); UV (CH3 OH) lambdamax 254.5, 278.0 (sh); 1 H NMR (DMSO-d6) delta 12.07, 11.78 (NH, s, 2H, D2 O exchangeable), 8.14 (s, H, 8-H), 5.53 (s, 2H, OCH2 N), 4.11-3.94 (m, 5H, (OCH2 CH)2 CH), 2.18 (s, 3H, AcN), 1.88 (s, 6H, AcO). Compound 10: mp 176°-178°; Rf 0.61 (CH3 OH:CHCl3 =1:9); UV (CH3 OH) lambdamax 261.5 nm; 1 H NMR (DMSO-d6) delta 12.18, 11.63 (s, 2H, NH, D2 O exchangeable), 8.38 (s, 1H, 8-H), 5.73 (s, 2H, OCH2 N), 4.14-3.92 (m, 5H, (OCH2 CH)2 CH), 2.17 (s, 3H, AcN), 1.88 (s, 6H, AcO).

Reference： [1]Patent: US5583225,1996,A

5
[ 86357-14-4 ]
[ 88110-89-8 ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; In ISOPROPYLAMIDE; at 50 - 75℃; for 3 - 48h;	Step (a) Preparation of 2-(2-amino-1,6 dihydro-6-oxo-purine-9-yl)-methoxy-3 acetoxy-1- propanol. 2(2-acetamido, 1,6-dihydro-6-oxo purine-9-yl)-methoxy-1,3-propane diol diactate (Triacetyl ganciclovir)(100gms) was stirred in N,N-dimethyl acetamide (200ml) and piperidine (200ml). Reaction mass was heated at 50-55 C for 48 hrs. After cooling this reaction mass to 25 °C, Hexane (1ltr.) was added and stirred for 30 min. and allowed to settle. Upper hexane layer was removed and Acetone (20)ml was added and stirred further. Hexane (500ml) was added while stirring and resulting solid was filtered and dried under vacuum at 50 °C to get 70gms of titled compound. Example 2. Preparation of 2-(2-amino 1,6 dihydro-6oxo-purine -9-yl)-methoxy -3 acetoxy-1-propanol. Triacetyl ganciclovir (50gms) was stirred in N,N-dimethyl acetamide (200ml) and piperidine (200 ml) . Reaction mass was heated at 75 C for 3 hrs. The reaction mass was cooled to 25 °C and Hexane (1ltr.) was added and stirred for 30 min. and allowed to settle. Upper hexane layer was removed and Acetone (20)ml was added and stirred further. Hexane (500ml) was added while stirring and resulting solid was filtered and dried under vacuum at 50 °C to get 40 gms of titled compound, which was then converted to valganciclovir following the reaction conditions as mentioned step-b to step-d of Example 1.
	With piperidine; at 50 - 55℃; for 48h;	Example 3 Triacetyl ganciclovir (100gms) was stirred with piperidine (400 ml). Reaction mass was heated at 50-55 °C for 48 hrs. The reaction mass was cooled to 25°C and Heptane (21tr.) was added and stirred for 30 min. and allowed to settle. Upper heptane layer was removed and Isopropyl alcohol (50) ml was added and stirred further. Heptane (1ltr.) was added while stirring and resulting solid was filtered and dried under vacuum at 50 °C to get 80 gms of 2-(2-aminol,6-dihydro-6oxo-purine-9-yl)-methoxy-3-acetoxy-1 propanol, which was the converted to valganciclovir following the reaction conditions as mentioned in step-b to step-d of Example 1.
	With morpholine; In ISOPROPYLAMIDE; at 70 - 75℃; for 48h;	Example 5. Triacetyl ganciclovir (100gms) was stirred with N,N-dimethyl acetamide (400ml) and morpholine (100 ml). Reaction mass was heated at 70-75 C for 48 hrs. The reaction mass was cooled to 25 °C and Hexane (21tr.) was added and stirred for 30 min. and allowed to settle. Upper hexane layer was removed and Acetone (40ml was added and stirred further. Hexane (1ltr.) was added while stirring and resulting solid was filtered and dried under vacuum at 50°C to get 70gms of 2-(2-aminol,6-dihydro-6oxo-purine-9-yl)-methoxy-3-acetoxy-1 propanol, which was then converted to valganciclovir following the reaction conditions as mentioned in step-b to step-d of Example 1.

	With piperazine; In ISOPROPYLAMIDE; at 70 - 75℃; for 48h;	Example 4.Triacetyl ganciclovir (100gms) was stirred with N,N-dimethyl acetamide (400ml) and piperazine (100gms). Reaction mass was heated at 70-75 °C for 48 hrs. The reaction mass was cooled to 25 °C and Hexane (2ltr.), was added and stirred for 30 min. and allowed to settle. Upper hexane layer was removed and Acetone (50)ml was added and stirred further. Hexane (1 ltr.) was added while stirring and resulting solid was filtered and dried under vacuum at 50 °C to get 75 gms of 2-(2-amino1,6-dihydro-6oxo-purine-9-yl)-methoxy-3-acetoxy-1 propanol, which was then converted to valganciclovir following the reaction conditions as mentioned in step-b to step-d of Example 1.
	With piperidine; N,N-dimethyl acetamide; at 50 - 75℃; for 3 - 48h;Product distribution / selectivity;	Example: 1 Step (a) Preparation of 2-(2-amino-1,6 dihydro-6-oxo-purine -9-yl)-methoxy-3 acetoxy-1-propanol 2(2-acetamido, 1,6-dihydro-6-oxo purine-9-yl)-methoxy-1,3-propane diol diactate (Triacetyl ganciclovir)(100 gms) was stirred in N,N-dimethyl acetamide (200 ml) and piperidine (200 ml). Reaction mass was heated at 50-55 C for 48 hrs. After cooling this reaction mass to 25° C., Hexane (1 ltr.) was added and stirred for 30 min. and allowed to settle. Upper hexane layer was removed and Acetone (20)ml was added and stirred further. Hexane (500 ml) was added while stirring and resulting solid was filtered and dried under vacuum at 50° C. to get 70 gms of titled compound. Example 2 Preparation of 2-(2-amino1,6 dihydro-6oxo-purine-9-yl)-methoxy-3 acetoxy-1-propanol Triacetyl ganciclovir (50 gms) was stirred in N,N-dimethyl acetamide (200 ml) and piperidine (200 ml). Reaction mass was heated at 75 C for 3 hrs. The reaction mass was cooled to 25° C. and Hexane (1 ltr.) was added and stirred for 30 min. and allowed to settle. Upper hexane layer was removed and Acetone (20)ml was added and stirred further. Hexane (500 ml) was added while stirring and resulting solid was filtered and dried under vacuum at 50° C. to get 40 gms of titled compound, which was then converted to valganciclovir following the reaction conditions as mentioned step-b to step-d of Example 1
	With piperidine; at 50 - 55℃; for 48h;Product distribution / selectivity;	Example 3 Triacetyl ganciclovir (100 gms) was stirred with piperidine (400 ml). Reaction mass was heated at 50-55° C. for 48 hrs. The reaction mass was cooled to 25° C. and Heptane (2 ltr.) was added and stirred for 30 min. and allowed to settle. Upper heptane layer was removed and Isopropyl alcohol (50) ml was added and stirred further. Heptane (1 ltr.) was added while stirring and resulting solid was filtered and dried under vacuum at 50° C. to get 80 gms of 2-(2-amino1,6-dihydro-6oxo-purine-9-yl)-methoxy-3-acetoxy-1 propanol, which was the converted to valganciclovir following the reaction conditions as mentioned in step-b to step-d of Example 1.
	With morpholine; N,N-dimethyl acetamide; at 70 - 75℃; for 48h;Product distribution / selectivity;	Triacetyl ganciclovir (100 gms) was stirred with N,N-dimethyl acetamide (400 ml) and morpholine (100 ml). Reaction mass was heated at 70-75 C for 48 hrs. The reaction mass was cooled to 25° C. and Hexane (2 ltr.) was added and stirred for 30 min. and allowed to settle. Upper hexane layer was removed and Acetone (40 ml was added and stirred further. Hexane (1 ltr.) was added while stirring and resulting solid was filtered and dried under vacuum at 50° C. to get 70 gms of 2-(2-amino1,6-dihydro-6oxo-purine-9-yl)-methoxy-3-acetoxy-1 propanol, which was then converted to valganciclovir following the reaction conditions as mentioned in step-b to step-d of Example 1.
	With piperazine; N,N-dimethyl acetamide; at 70 - 75℃; for 48h;Product distribution / selectivity;	Example 4 Triacetyl ganciclovir (100 gms) was stirred with N,N-dimethyl acetamide (400 ml) and piperazine (100 gms). Reaction mass was heated at 70-75° C. for 48 hrs. The reaction mass was cooled to 25° C. and Hexane (2 ltr.) was added and stirred for 30 min. and allowed to settle. Upper hexane layer was removed and Acetone (50)ml was added and stirred further. Hexane (1 ltr.) was added while stirring and resulting solid was filtered and dried under vacuum at 50° C. to get 75 gms of 2-(2-amino1,6-dihydro-6oxo-purine-9-yl)-methoxy-3-acetoxy-1 propanol, which was then converted to valganciclovir following the reaction conditions as mentioned in step-b to step-d of Example 1.

Reference： [1]Patent: EP1837336,2007,A1 .Location in patent: Page/Page column 10-11
[2]Patent: EP1837336,2007,A1 .Location in patent: Page/Page column 11
[3]Patent: EP1837336,2007,A1 .Location in patent: Page/Page column 11
[4]Patent: EP1837336,2007,A1 .Location in patent: Page/Page column 11
[5]Patent: US2007/225305,2007,A1 .Location in patent: Page/Page column 7
[6]Patent: US2007/225305,2007,A1 .Location in patent: Page/Page column 7
[7]Patent: US2007/225305,2007,A1 .Location in patent: Page/Page column 8
[8]Patent: US2007/225305,2007,A1 .Location in patent: Page/Page column 7-8

Yield	Reaction Conditions	Operation in experiment
	In Isopropyl acetate; acetonitrile; at 20℃; for 0.5h;Purification / work up;	Example 1:Preparation of N2-acetyl-9-(l,3-diacetoxy-2-propoxymethyl) guanineA mixture of diacetyl guanine (100 gm), dimethylformamide (300 ml), 2- acetoxymethoxy-l,3-diacetoxy propane (180 gm) and ethane sulfonic acid (1.07 gm) at 25 to 30°C. The mixture was slowly heated to 100 to 110°C and maintained for 6 hours at 100 to 110°C. The reaction mass was distilled off completely under vacuum at 100 to 110°C and cooled to 25 to 30°C. To the reaction mass was added 1 ,2- dimethoxy ethane (240 ml) and stirred for 30 minutes, filtered. The solid obtained was washed with 1 ,2-dimethoxy ethane and dried at 60°C to obtain 120 gm of a mixture containing N 2 -acetyl- 7-(l, 3 -diacetoxy-2-propoxymethyl)guanine and N 2 - acetyl-9-(l, 3 -diacetoxy-2-propoxymethyl) guanine (N-7 and N-9 isomers) (52percent of N- 9 isomer and 41.7percent of N-7 isomer).To the above mixture was added acetic acid (110 ml) and acetonitrile (550 ml) at 25 to 30°C to obtain a reaction mass having a pH of 4.0 to 5.0. The reaction mass was cooled to -5 to -10°C and stirred for 3 hours at -5 to -10°C. The separated solid was filtered, washed with chilled acetonitrile and the solid was dried at 60°C for 4 hours to obtain 40 gm of N2-acetyl-9-(l ,3-diacetoxy-2-propoxymethyl)guanine.N2-acetyl-9-(l,3-diacetoxy-2-propoxymethyl)guanine (40 gm) was dissolved in acetonitrile (40 ml) and isopropyl acetate (200 ml) at room temperature. The contents were stirred for 30 minutes at room temperature, filtered. The solid obtained was washed with isopropyl acetate and dried at 60°C for 4 hours to obtain 38 gm of N2-acetyl-9-(l,3-diacetoxy-2-propoxymethyl)guanine (High performance liquid chromatography (HPLC) Purity: 99.4percent; 0.05percent N-7 isomer).

7
[ 86357-14-4 ]
ganciclovir [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; water; In methanol; at 25 - 30℃; for 48h;Industry scale;Product distribution / selectivity;	Example 4:Preparation of ganciclovir anhydrous crystalline form HIN2-acetyl-9-(l,3-diacetoxy-2-propoxymethyl)guanine (2 Kg) was dissolved in methanol (16 L) and aqueous ammonia (16 L) at 25 to 30°C. The contents were maintained for 48 hours at 25 to 30°C, filtered. The solid obtained was washed with methanol and dried at 65°C for 9 hours to obtain 1 Kg of ganciclovir anhydrous crystalline form H 1.

Reference： [1]Patent: WO2011/114336,2011,A1 .Location in patent: Page/Page column 10

8
[ 82410-32-0 ]
[ 108-24-7 ]
[ 86357-14-4 ]