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

HRID 133560

反応式

HRID 133560 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-34382c61fea44e9f981f766d1eb53c37
出典データセット
uspto-grants-2008_06
特許番号
US07390830B1

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