Dimethyl Ether → (3R)-4-Amino-3-[4-chloro-3-(3-hydroxyphenyl)phenyl]butanoic acid hydrochloride

HRID 1799208

반응식

HRID 1799208 반응식
C[O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[CH:14]=[C:15]([C@@H:20]2[CH2:24][NH:23][C:22](=[O:25])[CH2:21]2)[CH:16]=[CH:17][C:18]=1[Cl:19].C[O:27]C>>[ClH:19].[NH2:23][CH2:24][C@@H:20]([C:15]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([OH:2])[CH:4]=2)[CH:14]=1)[CH2:21][C:22]([OH:25])=[O:27]

참가 물질

4

반응물 3

HCID 8254Dimethyl EtherHCID 2734370(3-Methoxyphenyl)boronic acidHCID 66724952(4R)-4-(3-bromo-4-chlorophenyl)pyrrolidin-2-one

생성물 1

HCID 66724800(3R)-4-Amino-3-[4-chloro-3-(3-hydroxyphenyl)phenyl]butanoic acid hydrochloride

실험 절차

Following the cross-coupling procedure according to Example 25 using 3-methoxyphenyl boronic acid and (4R)-4-(3-bromo-4-chlorophenyl)pyrrolidin-2-one followed by hydrolysis of the methyl ether using 48% HBr provided the title compound (34). 1H-NMR (400 MHz, CD3OD): δ 2.67-2.73 (dd, J=16.4, 6.4 Hz, 1H), 2.80-2.85 (dd, J=16.4, 7.6 Hz, 1H), 3.19-3.25 (dd, J=12.4, 12.0 Hz, 1H), 3.32-3.37 (m, 1H), 3.39-3.47 (m, 1H), 6.79-6.81 (m, 1H), 6.85-6.87 (m, 2H), 7.21-7.25 (m, 1H), 7.28-7.33 (m, 2H), 7.48-7.50 (d, J=8 Hz, 1H); MS (ESI) m/z 306.14 (M+H)+.

출처 및 근거

ORD 기록
ord-68b95ea487a34606981b7e29fa184205
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344028B2

연결된 노트

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