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

HRID 477129Notes

Reaction equation

HRID 477129 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:26])[C:20]2[N:21]=[C:22]([CH3:25])[S:23][CH:24]=2)[CH3:16])=[CH:10][CH:9]=1)[CH3:7])([O:3][CH3:4])=[O:2].[C:27]([O:31][CH3:32])(=[O:30])[CH:28]=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]([CH3:25])[S:23][CH:24]=3)[O:26][CH:28]2[C:27]([O:31][CH3:32])=[O:30])[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 53815041N-[2-(4-(2-Carbomethoxy-1-methylethenyl)phenyl)-1-methylethyl]-2-hydroxy-2-(2-methyl-thiazol-4-yl)ethanamine

Product 1

HCID 54350907Methyl 3-[2-(4-(2-Carbomethoxy-1-methylethenyl)phenyl)-1-methylethyl]-5-(2-methyl-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-methylethyl]-2-hydroxy-2-(2-methyl-thiazol-4-yl)ethanamine with methyl glyoxylate, followed by purification of the base on a silica gel column using petroleum ether/ethyl acetate=7:3 as eluant.

Workup

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

Sources & evidence

ORD record
ord-2099f2ad7e0b4c44b013d3bb5eb92745
Source dataset
uspto-grants-1989_12
Patent number
US04886814

Reaction notes

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