Trifluoroacetic acid → Trifluoroacetic acid

HRID 473524Notes

Reaction equation

HRID 473524 reaction equation
C(OC([NH:8][C@@H:9]([CH2:38][C:39]1[S:40][CH:41]=[CH:42][CH:43]=1)[C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]1[CH:19]=[C:20]([CH:35]=[CH:36][CH:37]=1)[O:21][CH:22]1[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]1)=[O:11])=O)(C)(C)C.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>ClCCl>[NH2:8][C@@H:9]([CH2:38][C:39]1[S:40][CH:41]=[CH:42][CH:43]=1)[C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]1[CH:37]=[CH:36][CH:35]=[C:20]([O:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:19]=1)=[O:11].[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67203078HCID 67203078, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 52919719HCID 52919719, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of the purified (S)-tert-butyl 4-(3-(5-(2-(tert-butoxycarbonylamino)-3-(thiophen-2-yl)propanamido)pent-1-ynyl)phenoxy)piperidine-1-carboxylate (0.26 g, 0.47 mmol) in dichloromethane (1.6 ml) was added TFA (0.4 ml) and the resulting mixture was stirred at room temperature for 1 hr. The resulting solution was concentrated and the residue purified over Gilson HPLC to yield (S)-2-amino-N-(5-(3-(piperidin-4-yloxy)phenyl)pent-4-ynyl)-3-(thiophen-2-yl)propanamide as its corresponding TFA salt, as a deep colored oil. MH+ 412.25. 1H NMR (300 MHz, DMSO), δ: 8.50 (1H, d), 8.23 (1H, s), 7.43 (1H, d), 7.30 (1H, m), 6.90 (3H, m), 4.65 (1H, m), 3.96 (1H, m), 2.96-3.30 (8H, m), 2.35 (2H, m), 2.10 (2H, m), 1.60-1.80 (4H, m)

Workup

  1. concentrationThe resulting solution was concentrated
  2. customthe residue purified over Gilson HPLC

Sources & evidence

ORD record
ord-9fd1103331504822b7b95fbc0aecad06
Source dataset
uspto-grants-2014_01
Patent number
US08633322B2

Reaction notes

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