Potassium Carbonate → 3-{[3-Chloro-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophen-5-ylmethyl]-amino}-propionic acid tert-butyl ester

HRID 2353372

Reaction equation

Br[CH2:2][C:3]1[CH:28]=[CH:27][C:6]2[S:7][C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[C:13]([C:23]([F:26])([F:25])[F:24])[CH:12]=3)=[C:9]([Cl:10])[C:5]=2[CH:4]=1.Cl.[C:30]([O:34][C:35](=[O:39])[CH2:36][CH2:37][NH2:38])([CH3:33])([CH3:32])[CH3:31].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[C:30]([O:34][C:35](=[O:39])[CH2:36][CH2:37][NH:38][CH2:2][C:3]1[CH:28]=[CH:27][C:6]2[S:7][C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[C:13]([C:23]([F:26])([F:25])[F:24])[CH:12]=3)=[C:9]([Cl:10])[C:5]=2[CH:4]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-bromomethyl-3-chloro-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene (50 mg, 0.104 mmol) in DMF (1 mL) are added β-alanine tert-butyl ester hydrochloride (19 mg, 1 eq.) and K2CO3 (68 mg, 5 eq.). The mixture is stirred at 50° C. overnight. The mixture is diluted with EtOAc (40 mL), washed with 10% aqueous Na2S2O3, brine, dried over MgSO4, filtered, and concentrated. The mixture is purified by column chromatography (EtOAc/Hexane, gradient) to give 43 mg of 3-{[3-chloro-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophen-5-ylmethyl]-amino}-propionic acid tert-butyl ester in 76% yield.

Workup

washwashed with 10% aqueous Na2S2O3, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe mixture is purified by column chromatography (EtOAc/Hexane, gradient)

Sources & evidence

ORD record: ord-e6a1f26314a7438da9d6c59b2b825bed
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750021B2

Linked notes

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