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[4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid 2-tert-butoxycarbonylamino-ethyl ester → [4-(4-Aminobutyl)phenoxy]acetic acid 2-tert-butoxycarbonylaminoethyl ester ethyl acetate

HRID 1175723
ノート
印刷プレビュー

反応式

HRID 1175723 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12](=[O:36])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25]C(OCC2C=CC=CC=2)=O)=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.C(OCC)(=O)C.ClCCl.[OH-].[OH-].[Pd+2]>[CH2:10]([O:11][C:12](=[O:36])[CH3:13])[CH3:9].[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12](=[O:36])[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 1

HCID 67350250[4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid 2-tert-butoxycarbonylamino-ethyl ester

生成物 1

HCID 67351832[4-(4-Aminobutyl)phenoxy]acetic acid 2-tert-butoxycarbonylaminoethyl ester ethyl acetate収率 137.5%

試薬・触媒・溶媒 4

HCID 176Acetic Acid触媒HCID 9942167Palladium hydroxide触媒HCID 6344Dichloromethane
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A solution of [4-(4-benzyloxycarbonylaminobutyl)phenoxy]acetic acid 2-tert-butoxycarbonylaminoethyl ester 44a (162 mg, 0.32 mmol) and acetic acid (3 drops) in ethyl acetate (3 mL) and dichloromethane (6 mL) was stirred at room temperature for 16 h under hydrogen atmosphere in the presence of palladium hydroxide on activated charcoal (80 mg, 60% wet). The catalyst was removed by suction filtration and the liquid filtrate was concentrated in vacuo to give [4-(4-aminobutyl)phenoxy]acetic acid 2-tert-butoxycarbonylaminoethyl ester ethyl acetate 45a as an off-white solid (100 mg, 84% yield) which was used directly without purification. m/z (ESI) 367 [C19H30N2O5+H]+.

後処理

  1. customThe catalyst was removed by suction filtration
  2. concentrationthe liquid filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-2c7389fcf1204a2f8ccaca2b468aa685
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07842697B2

反応ノート

読み込み中…

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