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

HRID 1527374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527374
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-713ae00e72574733a598a1be9e86b689
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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