| 97% |
|
To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H20 (15 mL) was added ClC02Me (1.74 mL, 22.55 mmol) dropwise at 0C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HC1. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2CI2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. XH NMR (400 MHz, CDC13) delta 4.19 (s, 1H), 3.92-3.97 (m, 1H), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13N05: 191; found: 190 (M-H) |
| 97% |
|
Cap-86 Me0(2S,3R)-3-Methoxy-2-(methoxycarbonylamino)butanoic acid[00213] To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H20 (15 mL) was added ClC02Me (1.74 mL, 22.55 mmol) dropwise at 0 C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HC1. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2C12 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. XH NMR (400 MHz, CDC13) 5 4.19 (s, 1H), 3.92-3.97 (m, 1H), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LC-MS: Anal. Calcd. for C7H13N05: 191; found: 190 (M-H)". |
| 97% |
With sodium hydroxide; In water; at 0℃; for 12.0h; |
To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H20 (15 mL) was added ClC02Me (1.74 mL, 22.55 mmol) dropwise at 0C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HCl. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2CI2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. 1HNMR (400 MHz, CDC13) delta 4.19 (s, 1H), 3.92-3.97 (m, 1H), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13N05: 191; found: 190 (M-H)". |
| 97% |
|
To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H2O (15 mL) was added ClCO2Me (1.74 mL, 22.55 mmol) dropwise at 00C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HCl. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2Cl2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. 1HNMR (400 MHz, CDCl3) delta 4.19 (s, IH), 3.92-3.97 (m, IH), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13NO5: 191; found: 190 (M-H)". |
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To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H2O (15 mL) was added ClCO2Me (1.74 mL, 22.55 mmol) dropwise at 0 C. The mixture was allowed to stir for 12 h and acidified to pH 1 using 1N HCl. The aqueous phase was extracted with EtOAc and (2×250 mL) and 10% MeOH in CH2Cl2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. 1H NMR (400 MHz, CDCl3) delta4.19 (s, 1H), 3.92-3.97 (m, 1H), 3.66 (s, 3H), 1.17 (d, J=7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13NO5: 191; found: 190 (M-H)-. |
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To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H20 (15 mL) was added ClC02Me (1.74 mL, 22.55 mmol) dropwise at 0 C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HC1. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2CI2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. 1H NMPv (400 MHz, CDCI3) delta 4.19 (s, 1H), 3.92-3.97 (m, 1H), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13N05: 191; found: 190 (M-H)-. |
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O-Methyl-L-threonine (25 g, 0.19 mol) was dissolved in 1,4-dioxane (125 mL) and cooled to 0 C. An aq 2 M NaOH (22.5 g, 0.56 mol, 3 equiv) solution was then added to the reaction mixture followed by methyl chloroformate (17.4 mL, 0.22 mol, 1.2 equiv) at the same temperature. The reaction mixture was warmed to rt and stirred for 16 h. The reaction mixture was washed with ethyl acetate (500 mL). The aq layer was acidified with 3 N HCl (up to pH 2) and extracted with ethyl acetate (3×250 mL). The combined organic layers were dried over Na2SO4 and concentrated to afford the crude product (23 g). Ethyl acetate (46 mL) was added to the crude product and heated at 80 C. to obtain a clear solution. This solution was then cooled to 0 C. The solid obtained was filtered and dried to afford the desired pure product (21) (18.75 g). |
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With sodium hydroxide; In water; at 20℃; for 12.0h;Sealed tube; Cooling with ice; |
Weigh 3.0gO- methyl -L- threonineAnd 0.902 g of sodium hydroxideIn a 100 mL dry vial,15 mL of water was added,0 underAfter adding 1.74 mL of methyl chloroformate,It was stirred under ice-naturally warmed to room temperature,Reaction 12h,After completion of the reaction,The reaction solution was adjusted to pH 1 with 1N HCl solution,Ethyl acetate extraction (5 x 100 mL) was added,The organic phase was dried,filter,Concentrated to give the title compound,Directly for the next reaction. |
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