3-[2-Methyl-5-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-benzoic acid methyl ester → 3-Oxo-3-[3-[2-methyl-5-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-phenyl]-propionic acid tert-butyl ester

HRID 1265633Notes

Reaction equation

HRID 1265633 reaction equation
CO[C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[C:12]([CH3:23])[S:13][C:14]=2[CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[CH:5]=1.[C:25]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[CH3:26].[Li]>>[C:29]([O:28][C:25](=[O:27])[CH2:26][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[C:12]([CH3:23])[S:13][C:14]=2[CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[CH:5]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

3

Reactant 2

HCID 696890913-[2-Methyl-5-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-benzoic acid methyl esterHCID 86586795Lithium Tert-butyl Acetate

Product 1

HCID 696876593-Oxo-3-[3-[2-methyl-5-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-phenyl]-propionic acid tert-butyl ester

Procedure

3-[2-Methyl-5-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-benzoic acid methyl ester was treated with lithium tert.-butyl acetate according to the general procedure K (method b) to give crude 3-oxo-3-[3-[2-methyl-5-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-phenyl]-propionic acid tert-butyl ester (5.45 g) as a pale-yellow oil.

Sources & evidence

ORD record
ord-c213369223be4e39b729c1f57065b9bf
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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