4-Ethoxybenzaldehyde → (4S)-3-[(3R,2S)-3-(4-ethoxyphenyl)-3-hydroxy-2-isopropoxypropanoyl]-4-benzyl-1,3-oxazolan-2-one

HRID 1985431Notes

Reaction equation

HRID 1985431 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)[CH3:2].[CH2:12]([C@H:19]1[CH2:23][O:22][C:21](=[O:24])[N:20]1[C:25](=[O:31])[CH2:26][O:27][CH:28]([CH3:30])[CH3:29])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([C@@H:8]([OH:9])[C@H:26]([O:27][CH:28]([CH3:30])[CH3:29])[C:25]([N:20]2[C@@H:19]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:23][O:22][C:21]2=[O:24])=[O:31])=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 248344-EthoxybenzaldehydeHCID 59997951(4S)-4-benzyl-3-(2-isopropoxyacetyl)oxazolidin-2-one

Product 1

HCID 57719757(4S)-3-[(3R,2S)-3-(4-ethoxyphenyl)-3-hydroxy-2-isopropoxypropanoyl]-4-benzyl-1,3-oxazolan-2-oneYield 105.4%

Procedure

Under the similar conditions to those described in Production example 332a), 2.4 g of 4-ethoxybenzaldehyde and 5.6 g of (4S)-4-benzyl-3-(2-isopropoxyacetyl)-1,3-oxazolidin-2-one were reacted, to give 7.2 g of (4S)-3-[(3R,2S)-3-(4-ethoxyphenyl)-3-hydroxy-2-isopropoxypropanoyl]-4-benzyl-1,3-oxazolan-2-one as a colorless solid.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c122805ea83c4a2c942bc278ceb737ab
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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