Trifluoroacetic acid → HCID 118157745, compound

HRID 1779230Notes

Reaction equation

HRID 1779230 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][S:42]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])(=[O:44])=[O:43])[C@@:22]([OH:33])([CH2:30][CH2:31][CH3:32])[C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][S:42]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])(=[O:44])=[O:43])[C@@:22]([OH:33])([CH2:30][CH2:31][CH3:32])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90060227HCID 90060227, compound

Product 1

HCID 118157745HCID 118157745, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-10-(octane-1-sulfonylamino)-2-propyl-dec-4-enoate (35.0 mg, 0.0467 mmol) was dissolved in dichloromethane (1.0 mL), and trifluoroacetic acid (1.0 mL, 13.6 mmol) was then added at room temperature. The mixture was stirred for 75 minutes, and then concentrated under reduced pressure. The resulting crude product was purified by preparative HPLC to obtain 29.1 mg (0.0420 mmol, 90% yield) of the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-bea88e5e5c634f1ba10c93c774bb7b1f
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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