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

HRID 1265629Notes

Reaction equation

HRID 1265629 reaction equation
CO[C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[S:11][C:12]([CH2:23][CH2:24][CH3:25])=[C:13]([CH2:15][O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[N:14]=2)[CH:5]=1.[C:27]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])[CH3:28].[Li]>>[C:31]([O:30][C:27](=[O:29])[CH2:28][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[S:11][C:12]([CH2:23][CH2:24][CH3:25])=[C:13]([CH2:15][O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[N:14]=2)[CH:5]=1)([CH3:34])([CH3:33])[CH3:32]

Participants

3

Reactant 2

HCID 696888463-[5-Propyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-benzoic acid methyl esterHCID 86586795Lithium Tert-butyl Acetate

Product 1

HCID 696881943-Oxo-3-[3-[5-propyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-phenyl]-propionic acid tert-butyl ester

Procedure

3-[5-Propyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-benzoic acid methyl ester (0.34 g) was treated with lithium tert.-butyl acetate according to the general procedure K (method b) to give crude 3-oxo-3-[3-[5-propyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-phenyl]-propionic acid tert-butyl ester (0.42 g) as a pale-yellow oil.

Sources & evidence

ORD record
ord-d70ae4b8f5534795b3668875ee51f4cb
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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