Trifluoroacetic acid → Trifluoroacetic acid

HRID 473516Notes

Reaction equation

HRID 473516 reaction equation
C(OC([NH:8][C@@H:9]([CH2:38][C:39]#[CH:40])[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:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>ClCCl>[NH2:8][C@@H:9]([CH2:38][C:39]#[CH:40])[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:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86653106(S)-tert-butyl 4-(3-(5-(2-(tert-butoxycarbonylamino)pent-4-ynamido)pent-1-ynyl)phenoxy)piperidine-1-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 52919595(S)-2-amino-N-(5-(3-(piperidin-4-yloxy)phenyl)pent-4-ynyl)pent-4-ynamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (S)-tert-butyl 4-(3-(5-(2-(tert-butoxycarbonylamino)pent-4-ynamido)pent-1-ynyl)phenoxy)piperidine-1-carboxylate (0.26 g, 0.47 mmol) in dichloromethane (4.0 ml), TFA (1.0 ml) was added. The resulting solution was stirred at room temperature for 1 hr, then concentrated. The resulting residue was purified over Gilson HPLC to yield the title compound as its corresponding TFA salt, as a white solid. MH+ 354.31

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was purified over Gilson HPLC

Sources & evidence

ORD record
ord-44c1f563802e4333806e24a46bbf6c82
Source dataset
uspto-grants-2014_01
Patent number
US08633322B2

Reaction notes

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