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

HRID 1527374Notes

Reaction equation

HRID 1527374 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-713ae00e72574733a598a1be9e86b689
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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