2-Bromo-4-phenylcyclohexan-1-one → HCID 68647835、化合物

HRID 1162588ノート

反応式

HRID 1162588 の反応式
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]

参加物

4

反応物 2

HCID 132483272-Bromo-4-phenylcyclohexan-1-oneHCID 86601761HCID 86601761、化合物

生成物 1

HCID 68647835HCID 68647835、化合物収率 98.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-172a384cc720402db10f86d6ed56fa20
出典データセット
uspto-grants-2010_10
特許番号
US07820704B2

反応ノート

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