Trifluoroacetic acid → (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester

HRID 1527374노트

반응식

HRID 1527374 반응식
C(OC([N:8]1[CH2:12][C@@H:11]([NH:13][C:14]([O:16][CH2:17][CH:18]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])[CH2:10][C@H:9]1[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:34]([O:33][C:31]([C@@H:9]1[CH2:10][C@H:11]([NH:13][C:14]([O:16][CH2:17][CH:18]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])[CH2:12][NH:8]1)=[O:32])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 68283347(2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

생성물 1

HCID 68283582(2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (7.3 g, 13.49 mmol) in CH2Cl2 (45 mL) was added TFA (5.1 mL, 67.5 mmol). The solution was stirred at RT overnight. The solvent was concentrated and the residue co-evaporated three times with CH2Cl2 to remove the excess of TFA. The crude residue was taken-up in diethylether and the resulting precipitate filtered-off to give the title compound as a white powder. MS (LC/MS): 443.2 [MH]+; tR (HPLC conditions a): 3.3 min; 1H-NMR (400 MHz, DMSO): δ (ppm) 9.84 (s, 1H), 9.14 (s, 1H), 7.90 (d, 2H), 7.68 (d, 2H), 7.62 (d, 1H), 7.45-7.33 (m, 9H), 5.28-5.21 (m, 2H), 4.59-4.54 (m, 1H), 4.41 (d, 2H), 4.26-4.16 (m, 2H), 3.46-3.41 (m, 1H), 3.16-3.11 (m, 1H), 2.64-2.58 (m, 1H).

후처리

  1. concentrationThe solvent was concentrated
  2. customto remove the excess of TFA

출처 및 근거

ORD 기록
ord-713ae00e72574733a598a1be9e86b689
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085555B2

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