Sodium Methoxide → (2S,3R)-3-(4-benzyloxy-2-trifluoromethyl-phenyl)-2-ethoxy-3-hydroxy-propionic acid methyl ester

HRID 1064950Notes

Reaction equation

HRID 1064950 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:39])[C@@H:15]([O:36][CH2:37][CH3:38])[C@@H:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:20][C:19]=1[C:32]([F:35])([F:34])[F:33])[OH:17])C1C=CC=CC=1.[CH3:40][O-:41].[Na+]>CO>[CH3:40][O:41][C:14](=[O:39])[C@@H:15]([O:36][CH2:37][CH3:38])[C@@H:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:20][C:19]=1[C:32]([F:34])([F:35])[F:33])[OH:17]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 69279901(S)-4-benzyl-3-[(2S,3R)-3-(4-benzyloxy-2-trifluoromethyl-phenyl)-2-ethoxy-3-hydroxy-propionyl]-oxazolidin-2-one

Product 1

HCID 69280418(2S,3R)-3-(4-benzyloxy-2-trifluoromethyl-phenyl)-2-ethoxy-3-hydroxy-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In analogy to the procedure described in example 1 b], (S)-4-benzyl-3-[(2S,3R)-3-(4-benzyloxy-2-trifluoromethyl-phenyl)-2-ethoxy-3-hydroxy-propionyl]-oxazolidin-2-one was treated with sodium methoxide in methanol to give (2S,3R)-3-(4-benzyloxy-2-trifluoromethyl-phenyl)-2-ethoxy-3-hydroxy-propionic acid methyl ester as colorless liquid. According to 1H-NMR spectroscopy, one single diastereomer was obtained.

Sources & evidence

ORD record
ord-e4330b52d3cf48c3a38d131613af18a5
Source dataset
uspto-grants-2005_11
Patent number
US06969725B2

Reaction notes

Loading…