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

HRID 1162588노트

반응식

HRID 1162588 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 68647835HCID 68647835, 화합물수율 98.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-172a384cc720402db10f86d6ed56fa20
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820704B2

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