Diethyl methylphosphonite → (4S)-3-benzyloxycarbonyl-4-{2-[ethoxy(methyl)phosphinyl]ethyl}-1,3-oxazolidin-5-one

HRID 233116

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH2:17]Br)[C:14](=[O:19])[O:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][P:21]([O:25]CC)[O:22][CH2:23][CH3:24]>>[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH2:17][P:21]([O:22][CH2:23][CH3:24])([CH3:20])=[O:25])[C:14](=[O:19])[O:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 85063Diethyl methylphosphonite

HCID 14103855(4S)-3-benzyloxycarbonyl-4-(2-bromoethyl)-1,3-oxazolidin-5-one

Product 1

HCID 14596286(4S)-3-benzyloxycarbonyl-4-{2-[ethoxy(methyl)phosphinyl]ethyl}-1,3-oxazolidin-5-oneYield 81.1%

Conditions

Temperature: 120 °C

Procedure

5.30 g (16.1 mmol) of (4S)-3-benzyloxycarbonyl-4-(2-bromomethyl)-1,3-oxazolidin-5-one (from Example 5) are mixed with 4.40 g (32.3 mmol) of diethyl methanephosphonite and the mixture is heated under argon for 6 hours at 120° C. The excess diethyl methanephosphonite is distilled off in high vacuum and the residue is purified by chromatography on silica gel (mobile phase: dichloromethane/acetonitrile). 4.64 g (81.1% of theory) of (4S)-3-benzyloxycarbonyl-4-{2-[ethoxy(methyl)phosphinyl]ethyl}-1,3-oxazolidin-5-one are obtained as a colorless oil. Analytical data:

Workup

distillationThe excess diethyl methanephosphonite is distilled off in high vacuum
customthe residue is purified by chromatography on silica gel (mobile phase: dichloromethane/acetonitrile)

Sources & evidence

ORD record: ord-477b041f09a44fa0b19b83abb4644b6d
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05591861

Linked notes

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