Trifluoroacetic acid → (R)-4-biphenyl-4-yl-3-(3-carboxy-propionylamino)-butyric acid ethyl ester

HRID 70865

반응식

HRID 70865 반응식
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C@H:6]([NH:20][C:21](OC(C)(C)C)=[O:22])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH3:2].C(O)(C(F)(F)F)=O.C1(=O)[O:41][C:39](=[O:40])[CH2:38][CH2:37]1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C@H:6]([NH:20][C:21](=[O:22])[CH2:37][CH2:38][C:39]([OH:41])=[O:40])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:12][CH:13]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acid2회HCID 7922Succinic anhydrideHCID 59607632(R)-ethyl 4-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)butanoate

생성물 1

HCID 49822223(R)-4-biphenyl-4-yl-3-(3-carboxy-propionylamino)-butyric acid ethyl ester수율 50.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (R)-4-biphenyl-4-yl-3-tert-butoxycarbonylamino-butyric acid ethyl ester (400 mg, 1.04 mmol) in DCM (10 mL) at room temperature is added TFA (2.009 mL, 26.1 mmol) and the mixture is stirred at room temperature for 1 hour. The mixture is concentrated under reduced pressure. To the obtained TFA salt in DCM (10 mL) at ice bath temperature is added succinic anhydride (125 mg, 1.25 mmol) and followed by TEA (0.363 mL, 2.61 mmol). The reaction is stirred at room temperature for 16 hours. The mixture is concentrated under reduced pressure. The obtained residue is purified by flash chromatography (silica gel, 2% to 5% EtOH/DCM) give (R)-4-biphenyl-4-yl-3-(3-carboxy-propionylamino)-butyric acid ethyl ester (200 mg). HPLC retention time=1.53 minutes (condition C); MS=384 (m+1).

후처리

  1. concentrationThe mixture is concentrated under reduced pressure
  2. stirringThe reaction is stirred at room temperature for 16 hours
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customThe obtained residue is purified by flash chromatography (silica gel, 2% to 5% EtOH/DCM)

출처 및 근거

ORD 기록
ord-d1bb9c9294a7440fa0cfad366f1f6fab
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822534B2

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