HCID 68752619, 화합물 → 2-(1-(3-Tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acid

HRID 333296노트

반응식

HRID 333296 반응식
C([O:8][C:9](=[O:37])[CH2:10][C:11]1([C:16]([NH:18][CH2:19][CH:20]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1>CCO.[Pd]>[C:24]([O:23][C:21](=[O:22])[CH:20]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=1)[CH2:19][NH:18][C:16]([C:11]1([CH2:10][C:9]([OH:37])=[O:8])[CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:17])([CH3:27])([CH3:25])[CH3:26]

참가 물질

4

반응물 1

HCID 68752619HCID 68752619, 화합물

생성물 1

HCID 687477812-(1-(3-Tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acid수율 45.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A suspension of tert-butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-2-(3,4-dichlorobenzyl)propanoate (81.2 mg, 0.148 mmol) and Pd/C (31.5 mg, 0.015 mmol) in EtOH (1 ml) was allowed to stir under hydrogen atmosphere (1 atm) for 6.5 hr. The reaction mixture was filtered, and the filter cake was washed with MeOH. The combined filtrate was concentrated under reduced pressure. The obtained residue was purified by RP-HPLC (X-Bridge C18, H2O (0.1% NH4OH)/CH3CN) to give 2-(1-(3-tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acid (30.6 mg); Retention time=1.30 minutes (condition B); MS (m+1)=458.2; 1H NMR (400 MHz, CDCl3, data for major rotamer) δ ppm 1.37 (s, 9H) 1.70-1.98 (m, 8H) 2.64-2.88 (m, 5H) 3.34-3.53 (m, 2H) 6.53-6.56 (m, 1H) 7.02-7.04 (m, 1H) 7.28 (d, J=2.0 Hz, 1H) 7.36 (d, J=8.0 Hz, 1H).

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake was washed with MeOH
  3. concentrationThe combined filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by RP-HPLC (X-Bridge C18, H2O (0.1% NH4OH)/CH3CN)

출처 및 근거

ORD 기록
ord-7a378b70347343958732246d0b67a657
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877815B2

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