Formic Acid → (R)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine

HRID 133560

반응식

HRID 133560 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:10]=1[C:11]([NH:13][CH2:14][C:15]([NH:17][C@@H:18]1[CH2:22][CH2:21][N:20](CC2C=CC(Cl)=CC=2)[CH2:19]1)=[O:16])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)=O>[OH-].[OH-].[Pd+2].CO>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:31][C:10]=1[C:11]([NH:13][CH2:14][C:15]([NH:17][C@@H:18]1[CH2:22][CH2:21][NH:20][CH2:19]1)=[O:16])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 284Formic AcidHCID 54203221(R)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]-1-(4-chlorobenzyl)pyrrolidine

생성물 1

HCID 54307129(R)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매

반응 조건

온도
50 °C

실험 절차

A mixture of (R)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]-1-(4-chlorobenzyl)pyrrolidine (6.3 g, 11.4 mmol) with Pd(OH)2 (1.68 g), formic acid (3.7 mL) and methanol (80 mL) was stirred at 50° C. overnight. The mixture was cooled to room temperature, and the palladium catalyst was then removed by filtration through Celite. The resulting filtrate was concentrated and purified by column chromatography [SiO2, ethyl acetate/methanol=(5:1) to (4:1)] to thereby provide (R)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine (4.42 g, 90%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 1.48 (s, 9H), 2.0-2.4 (m, 2H), 3.42-3.71 (m, 5H), 4.00-4.22 (m, 2H), 4.56 (br, 1H), 7.48 (d, J=9.0 Hz, 1H), 7.93 (s, 1H), 8.17 (br, 1H), 8.33 (d, J=9.0 Hz, 1H), 8.45 (br, 1H).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customthe palladium catalyst was then removed by filtration through Celite
  3. concentrationThe resulting filtrate was concentrated
  4. custompurified by column chromatography [SiO2, ethyl acetate/methanol=(5:1) to (4:1)] to thereby provide (R)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine (4.42 g, 90%) as a white solid

출처 및 근거

ORD 기록
ord-34382c61fea44e9f981f766d1eb53c37
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390830B1

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