Trifluoroacetic acid → HCID 118157434, compound

HRID 1779189Notes

Reaction equation

HRID 1779189 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][CH2:41][O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[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:7]=[CH:8][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][CH2:41][O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[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:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118260130HCID 118260130, compound

Product 1

HCID 118157434HCID 118157434, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-heptyloxy-2-hydroxy-2-propyl-undec-4-enoate (No. 6804256; 65.6 mg, 0.0956 mmol) was dissolved in dichloromethane (3.0 mL), and trifluoroacetic acid (1.0 mL) was added. The mixture was stirred at room temperature for 5.0 hours. The solvent was distilled off under reduced pressure. To the residue was added dichloromethane, and the solvent was again distilled off under reduced pressure. This operation was repeated twice. The residue was then purified by HPLC (water with 0.05% TFA-acetonitrile with 0.05% TFA) to obtain (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-heptyloxy-2-hydroxy-2-propyl-undec-4-enoic acid (No. 5500523; 19.3 mg, 32% yield).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionTo the residue was added dichloromethane
  3. distillationthe solvent was again distilled off under reduced pressure
  4. customThe residue was then purified by HPLC (water with 0.05% TFA-acetonitrile with 0.05% TFA)

Sources & evidence

ORD record
ord-94d7ab7d13634977ad93bc357fe9d250
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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