Trifluoroacetic acid → 3-[4-Hydroxy-2-(2-isopropoxycarbonylamino-ethyl)-phenyl]-propionic acid methyl ester

HRID 1181088ノート

反応式

HRID 1181088 の反応式
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH2:13][CH2:14][NH:15][C:16]([O:18][C:19](C)([CH3:21])[CH3:20])=[O:17].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH2:13][CH2:14][NH:15][C:16]([O:18][CH:19]([CH3:20])[CH3:21])=[O:17]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 589793153-[2-(2-Tert-butoxycarbonylamino-ethyl)-4-hydroxy-phenyl]-propionic acid methyl ester

生成物 1

HCID 589793233-[4-Hydroxy-2-(2-isopropoxycarbonylamino-ethyl)-phenyl]-propionic acid methyl ester収率 67%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 3-[2-(2-tert-butoxycarbonylamino-ethyl)-4-hydroxy-phenyl]-propionic acid methyl ester (282 mg, 0.876 mmol; Example 544, Step E) in CH2Cl2 (10 mL) at ambient temperature was treated with TFA (5.0 mL), stirred for 60 min, and concentrated. The residue in CH2Cl2 (10 mL) was treated with triethyl amine (2.0 mL) and iso-propyl chloroformate (0.97 mL, 1.0 M in toluene). The reaction mixture was stirred at ambient temperature for 16 h and concentrated. The crude material was purified using silica gel chromatography (50% EtOAc/hexanes) to yield the title compound (180 mg, 67%).

後処理

  1. concentrationconcentrated
  2. additionThe residue in CH2Cl2 (10 mL) was treated with triethyl amine (2.0 mL) and iso-propyl chloroformate (0.97 mL, 1.0 M in toluene)
  3. stirringThe reaction mixture was stirred at ambient temperature for 16 h
  4. concentrationconcentrated
  5. customThe crude material was purified

出典と根拠

ORDレコード
ord-595e2578ce7f45a2a473885d9bed79ee
出典データセット
uspto-grants-2007_10
特許番号
US07282501B2

反応ノート

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