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

HRID 1265626Notes

Reaction equation

HRID 1265626 reaction equation
CO[C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2([CH2:16][O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[CH:14]([CH3:15])[S:13][CH:12]=[N:11]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([CH2:16][O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[CH:14]([CH3:15])[S:13][CH:12]=[N:11]2)[CH:5]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

3

Reactant 2

HCID 696881293-[5-Methyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-benzoic acid methyl esterHCID 86586795Lithium Tert-butyl Acetate

Product 1

HCID 696892753-Oxo-3-[3-[5-methyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-phenyl]-propionic acid tert-butyl ester

Procedure

3-[5-Methyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-benzoic acid methyl ester (1.45 g) was treated with lithium tert.-butyl acetate according to the general procedure K (method b) to give crude 3-oxo-3-[3-[5-methyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-phenyl]-propionic acid tert-butyl ester (2.13 g) as a pale-yellow oil.

Sources & evidence

ORD record
ord-825c55e166b64c069f191309a9d28c9b
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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