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

HRID 1181088노트

반응식

HRID 1181088 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-595e2578ce7f45a2a473885d9bed79ee
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282501B2

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