Methyl chloroformate → HCID 11019395, compound

HRID 1979091Notes

Reaction equation

HRID 1979091 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].Cl[C:11]([O:13][CH3:14])=[O:12].[OH-].[Na+]>O>[OH:8][CH2:7][C@H:5]([NH:6][C:11]([O:13][CH3:14])=[O:12])[C:4]([O:3][CH3:2])=[O:9]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 11019395HCID 11019395, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 72.03 g L-serine-methylester hydrochloride in 400 ml of water were added at 0° C. 49.5 g of methyl chioroformate. The pH was kept at 6-7 by adding a 40% aqueous solution of sodium hydroxide. After 2½ h at 0° C. the mixture was extracted with 6 portions of ethyl acetate, the combined extracts were dried and evaporated to give 75.39 g (92%) of pure methyl 3-hydroxy-(S)-2-methoxycarbonylamino-propionate. IR (neat): 3380 m (NH, OH), 1720s, br. (C═O), 1535s (amide II). MS (EI): 178/20 (M+H+).

Workup

  1. extractionAfter 2½ h at 0° C. the mixture was extracted with 6 portions of ethyl acetate
  2. customthe combined extracts were dried
  3. customevaporated

Sources & evidence

ORD record
ord-27672705137c4b5aabd129cf78cbfe2a
Source dataset
uspto-grants-2001_05
Patent number
US06239296B1

Reaction notes

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