2-Bromo-1-(4-(propan-2-yl)phenyl)ethan-1-one → 4-{Cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}-butyric acid

HRID 1162581Notes

Reaction equation

HRID 1162581 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][CH2:5][CH2:6][N:7]([CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:8]([NH2:10])=[S:9].Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=1)=O>>[CH:11]1([N:7]([C:8]2[S:9][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=3)[N:10]=2)[CH2:6][CH2:5][CH2:4][C:3]([OH:2])=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 140427562-Bromo-1-(4-(propan-2-yl)phenyl)ethan-1-oneHCID 860798234-(1-Cyclopentyl-thioureido)-butyric acid methyl ester

Product 1

HCID 595202384-{Cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}-butyric acid

Procedure

4-{Cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}-butyric acid was prepared according to general procedure B using 4-(1-cyclopentyl-thioureido)-butyric acid methyl ester (70 mg, 0.3 mmol) and 2-bromo-4′-isopropylacetophenone (80.0 mg, 0.3 mmol). Purification (Silica gel, ethyl acetate/hexane 5:95) provided the ester, which was hydrolyzed following general procedure T. LCMS m/z: 374 (M+1)+.

Workup

  1. customPurification (Silica gel, ethyl acetate/hexane 5:95)

Sources & evidence

ORD record
ord-91940563f99e4a0f85d2cd6aec6003b4
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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