Trifluoroacetic acid → {(3S,5S)-5-[(R)-(1,2,3,4-Tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester trifluoroacetate

HRID 1481911Notes

Reaction equation

HRID 1481911 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:43])[NH:32][C@H:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36][CH2:35][CH2:34]1)=O)(C)(C)C.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>C(Cl)Cl>[F:47][C:46]([F:49])([F:48])[C:44]([OH:50])=[O:45].[CH:20]1[C:19]2[CH:18]([CH2:17][O:16][C:14](=[O:15])[NH:13][C@H:11]3[CH2:10][C@@H:9]([C:31](=[O:43])[NH:32][C@H:33]4[C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[CH2:36][CH2:35][CH2:34]4)[NH:8][CH2:12]3)[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57806828(2S,4S)-tert-butyl 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidine-1-carboxylate2×

Product 1

HCID 90220816{(3S,5S)-5-[(R)-(1,2,3,4-Tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (Intermediate 21) (9.5 g, 16.35 mmol) in DCM (50 mL) at 0° C. was added TFA (49 mL, 654.045 mmol) dropwise and the cooling bath removed. After 16 h the mixture was concentrated and the residue was triturated with ether to provide the title compound as an off white solid (9.55 g). LC-MS: 482 (M+H).

Workup

  1. customthe cooling bath removed
  2. concentrationAfter 16 h the mixture was concentrated
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-63bb92c369d449969b4422110e0c6faf
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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