Trifluoroacetic acid → HCID 131734847, compound

HRID 1779165Notes

Reaction equation

HRID 1779165 reaction equation
C(OC([NH:8][C@@H:9]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]#[C:32][CH3:33])=[CH:25][CH:24]=1)[C:10]([O:12][CH2:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])=O)(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>C(Cl)Cl>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[NH2:8][C@@H:9]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]#[C:32][CH3:33])=[CH:25][CH:24]=1)[C:10]([O:12][CH2:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118260105HCID 118260105, compound

Product 1

HCID 131734847HCID 131734847, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Oxo-2-phenyl-ethyl (S)-2-tert-butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionate (275 mg) was dissolved in methylene chloride (5.0 mL), and trifluoroacetic acid (1.0 mL) was added. The mixture was reacted with stirring for 30 minutes. After completing the reaction, the solvent was distilled off under reduced pressure. An appropriate amount (ca. 5 mL) of toluene was added and the mixture was concentrated in vacuo three times (azeotropic distillation) to obtain 290 mg of the target compound (LCMS m/z 352 (M+1) Rt 1.38 min.).

Workup

  1. customThe mixture was reacted
  2. customthe reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionAn appropriate amount (ca. 5 mL) of toluene was added
  5. concentrationthe mixture was concentrated in vacuo three times (azeotropic distillation)

Sources & evidence

ORD record
ord-345177e7ee944be28f04ce999e5f2a1a
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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