Trifluoroacetic acid → ((S)-5-amino-6-{(S)-2-[5-(4-fluoro-benzoyl)-pyridin-3-yl]pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 2093308Notes

Reaction equation

HRID 2093308 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:53])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([NH:45]C(OC(C)(C)C)=O)[C:23]([N:25]3[CH2:29][CH2:28][CH2:27][C@H:26]3[C:30]3[CH:31]=[N:32][CH:33]=[C:34]([C:36](=[O:44])[C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)[CH:35]=3)=[O:24])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:53])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([NH2:45])[C:23]([N:25]3[CH2:29][CH2:28][CH2:27][C@H:26]3[C:30]3[CH:31]=[N:32][CH:33]=[C:34]([C:36](=[O:44])[C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)[CH:35]=3)=[O:24])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58402903((S)-5-tert-butoxycarbonylamino-6-{(S)-2-[5-(4-fluoro-benzoyl)-pyridin-3-yl]-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 67339553((S)-5-amino-6-{(S)-2-[5-(4-fluoro-benzoyl)-pyridin-3-yl]pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((S)-5-tert-butoxycarbonylamino-6-{(S)-2-[5-(4-fluoro-benzoyl)-pyridin-3-yl]-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (I-1a) in dichloromethane (15 mL) was added trifluoroacetic acid (5 mL). After stirring for 45 minutes, the reaction mixture was concentrated in vacuo to afford crude ((S)-5-amino-6-{(S)-2-[5-(4-fluoro-benzoyl)-pyridin-3-yl]pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester as a dark amber residue.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b3e99406128a4b06ac3a342d789e1980
Source dataset
uspto-grants-2013_05
Patent number
US08445440B2

Reaction notes

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