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

HRID 70865

反応式

HRID 70865 の反応式
[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]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acid2 回HCID 7922Succinic anhydrideHCID 59607632(R)-ethyl 4-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)butanoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d1bb9c9294a7440fa0cfad366f1f6fab
出典データセット
uspto-grants-2014_09
特許番号
US08822534B2

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