2-Bromo-4-phenylcyclohexan-1-one → HCID 68647835, compound

HRID 1162588Notes

Reaction equation

HRID 1162588 reaction equation
Br[CH:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][C:3]1=O.[C:15]([O:19][C:20](=[O:32])[CH2:21][CH2:22][N:23]([CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[C:24]([NH2:26])=[S:25])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20](=[O:32])[CH2:21][CH2:22][N:23]([CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[C:24]1[S:25][C:2]2[CH2:7][CH:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:5][CH2:4][C:3]=2[N:26]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 132483272-Bromo-4-phenylcyclohexan-1-oneHCID 86601761HCID 86601761, compound

Product 1

HCID 68647835HCID 68647835, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 2-bromo-4-phenylcyclohexanone (2.30 mmol) and 3-(1-Cyclopentyl-thioureido)-propionic acid tert-butyl ester (257 mg, 0.945 mmol) were combined as in general procedure B (13 mL THF, 40° C., 15 h). After aqueous workup, the crude product was purified by silica gel chromatography (gradient, hexane→10% EtOAc-hexane) to afford 3-[cyclopentyl-(6-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amino]-propionic acid tert-butyl ester (398 mg). The ester was dissolved in CH2Cl2 (2 mL) and TFA (2 mL) was added. The reaction mixture was stirred at room temperature, until the starting material, was consumed by TLC. The volatiles were removed and the residue was dissolved in MeOH. NaOH solution (0.90 mmol) was added followed by half-saturated NaCl (20 mL). The aqueous layer was extracted with CH2Cl2 (3×15 mL) and dried over MgSO4 to provide 3-[Cyclopentylcyclopentyl-(6-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amino]-propionic acid. The sodium salt was prepared by general procedure J and triturated with hexane to yield 3-[cyclopentyl-(6-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amino]-propionic acid, sodium salt (336 mg) LCMS m/z: 372 (M+1)+.

Workup

  1. customAfter aqueous workup, the crude product was purified by silica gel chromatography (gradient, hexane→10% EtOAc-hexane)

Sources & evidence

ORD record
ord-172a384cc720402db10f86d6ed56fa20
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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