Acetic acid, 2-oxo-, methyl ester → Methyl 3-[2-(4-(2-carbomethoxy-1-methylethenyl)phenyl)-1-methylethyl]-5-(2-trifluoromethyl-thiazol-4-yl)-2-oxazolidine carboxylate

HRID 1451438Notes

Reaction equation

HRID 1451438 reaction equation
[C:1]([CH:5]=[C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([NH:17][CH2:18][CH:19]([OH:29])[C:20]2[N:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[S:23][CH:24]=2)[CH3:16])=[CH:10][CH:9]=1)[CH3:7])([O:3][CH3:4])=[O:2].[C:30]([O:34][CH3:35])(=[O:33])[CH:31]=O>>[C:1]([CH:5]=[C:6]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH:15]([N:17]2[CH2:18][CH:19]([C:20]3[N:21]=[C:22]([C:25]([F:27])([F:28])[F:26])[S:23][CH:24]=3)[O:29][CH:31]2[C:30]([O:34][CH3:35])=[O:33])[CH3:16])=[CH:12][CH:13]=1)[CH3:7])([O:3][CH3:4])=[O:2]

Participants

3

Reactant 2

HCID 70205Acetic acid, 2-oxo-, methyl esterHCID 53895654N-[2-(4-(2-Carbomethoxy-1-methylethenyl)phenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

Product 1

HCID 53740143Methyl 3-[2-(4-(2-carbomethoxy-1-methylethenyl)phenyl)-1-methylethyl]-5-(2-trifluoromethyl-thiazol-4-yl)-2-oxazolidine carboxylate

Procedure

Prepared by analogy to Example 18 by reaction of N-[2-(4-(2-carbomethoxy-1-methylethenyl)phenyl)-1-methyl-ethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)- ethanamine with methyl glyoxylate followed by purification of the base on a silica gel column using chloroform/petroleum ether/ethyl acetate=5:4.5:0.5 as eluant.

Workup

  1. customfollowed by purification of the base on a silica gel column

Sources & evidence

ORD record
ord-26ee87048e614cfa90812fe20d8a96d1
Source dataset
uspto-grants-1997_02
Patent number
US05604225

Reaction notes

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