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CAS No. : | 35320-22-0 | MDL No. : | MFCD00672501 |
Formula : | C3H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HQMLIDZJXVVKCW-UWTATZPHSA-N |
M.W : | 88.11 | Pubchem ID : | 446080 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; sodium hydrogencarbonate; In methanol; chloroform; water; | Step 2 3-Methyl-2-hydroxypyrazine <strong>[35320-22-0]D-alanine amide</strong>(7.5 g, 60.2 mmol) was suspended in MeOH (100 mL). H2 O (10 mL) was added to dissolve the solid. The solution was cooled to -30. Glyoxal (72.2 mmol, 8.28 mL of 40% weight solution) was added in one portion. 12.5 N NaOH (12 mL) was added dropwise over 20 minutes. The resulting mixture was stirred at -30 for 40 minutes then at room temperature for another 3 hours. The reaction mixture was placed in refrigerator overnight. The yellow suspension was cooled to 0 and then treated with concentrated HCl (15 mL) followed by NaHCO3 (12.3 g). The resulting neutral mixture was filtered through a frit. The filtrate was added to H2 O (12 mL) and concentrated to remove MeOH. The residue was treated with 100 mL MeOH and filtered to remove the salt. The filtrate was concentrated again to yield a tacky solid that was shaken with CHCl3 (100 mL). Just enough water was added to make the dark aqueous phase supernatant (~15 mL). This aqueous layer was extracted with CHCl3 (6*, 50 mL portions). The organic layers were combined and dried (MgSO4), filtered and concentrated to yield 3-methyl-2-hydroxypyrazine as an off-white solid. 1 H NMR (400 MHz, CDCl3) delta 12.52 (bs, 1H); 7.37 (d, 2H); 7.14 (d, 2H); 2.48 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; In ethanol; | Step 1 D-alanine amide D-alanine (10 g, 71.6 mmol) was dissolved in EtOH in a pressure vessel. The solution was cooled to -78. NH3 (l) (90 mL) was condensed into the reaction mixture. The pressure vessel was sealed and stirred at room temperature for 2 days. The excess ammonia was released from the vessel. The resulting suspension was concentrated to yield the title compound as a white solid which was dried under hi-vacuum for 16 hours overnight. 1 H NMR (400 MHz, CDCl3) delta (12.52 (bs, 1H); 7.37 (d, 1H); 7.14 (d, 1H); 2.49 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Analogously, starting from (4) and (R)-(-)-2-aminopropanamide, the R-enantiomer can be obtained (m.p. 170 C. dec.), [alpha]D225 -3.0 (C=1.1 DMF). | ||
K is --NH(CH2CH3) or is an aminoacyl residue selected from the group consisting of D-alanylamide, D-alanyl(OH), D-glutamyl(OH), | ||
T is --NH(CH2 CH3) or is an aminoacyl residue selected from the group consisting of D-alanylamide, N(R1)-L-alaninamide, N(R1)-D-alaninamide, D-serylamide, and azaglycylamide, |
J is --NH(CH2 CH3) or is an amino acyl residue selected from the group consisting of D-alaninamide, N-(R0)-D-alaninamide, N-(R0)-L-alaninamide, alpha-aza-glycinamide, D-serinamide, and | ||
J is --NH(CH2 CH3) or is an amino acyl residue selected from the group consisting of D-alaninamide, alpha-aza-glycinamide, D-serinamide, and | ||
D. Coupling of D-alanine amide with L-aspartic acid N-thiocarboxyanhydride The D-alanine amide provided in Part C, 1.1 g (5.1 mmole) is dissolved in 5 ml of tetrahydrofuran and 5 ml of water is added. The clear solution is cooled in ice and 0.89 g (5.1 mmole) of L-aspartic acid N-thiocarboxyanhydride is added in one portion. To this is added as required, 0.5M sodium hydroxide to maintain the mixture at pH 9. After stirring 30 minutes the reaction mixture is washed with ethyl ether, then ethyl acetate and the washes are discarded. The aqueous phase is acidified with dilute hydrochloric acid to pH 5.6 and evaporated to dryness at reduced pressure. The residue is taken up in hot methanol, filtered and the methanol evaporated. The residue is taken up again in hot methanol, filtered and the filtrate decolorized with activated carbon, filtered through diatomaceous earth and the filtrate is evaporated to obtain the crude product. The crude product is dissolved in hot water and filtered, concentrated under a stream of nitrogen to a small volume and cooled to precipitate the title compound. Use of D-2-aminobutyric acid, D-serine, D-valine or D-2-aminopentanoic acid in place of D-alanine in the procedure of Part A above and reacting the N-t-butoxycarbonyl-D-amino carbonyl-D-amino acids thus obtained in the procedures of Parts B, C and D, similarly provides the corresponding compounds of formula (I) wherein R is 3,5-dimethyl-1,2-dithiolan-4-yl and Ra is C2 H5, CH2 OH, (CH3)2 CH, or CH3 CH2 CH2, respectively. | ||
Xaa11 is a hydroxy group or an amino acid amide selected from the group consisting of D-alanylamide, D-alanylethylamide, azaglycylamide, glycylamide, glycylethylamide, serylamide, D-serylamide, | ||
A compound according to claim 1 wherein Xaa11 is selected from the group consisting of D-alanylamide, D-alanylethylamide, azaglycylamide, NH-cyclobutyl, NH-cycloheptyl, NH-ethyl, glycylamide, glycylethylamide, NH-hexyl, ... | ||
Xaa11 is a hydroxy group or an amino acid amide selected from the group consisting of: alanylamide, D-alanylamide, alanylethylamide, D-alanylethylamide, azaglycylamide, glycylamide, glycylethylamide, N-methyl-D-alanylamide, serylamide, ... | ||
A compound according to claim 1, wherein Xaa11 is selected from the group consisting of alanylamide, D-alanylamide, alanylethylamide, D-alanylethylamide, azaglycylamide, NH-cyclobutyl, NH-cycloheptyl, NH-ethyl, NH-glycyl, ... |