Trifluoroacetic acid → HCID 70562875, compound

HRID 1427215Notes

Reaction equation

HRID 1427215 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][C:16]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]2[C:17]=1[CH:18]=[CH:19][N:20]2[C:26]([C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)([CH2:31][CH3:32])[C:27]([O:29][CH3:30])=[O:28])=O)(C)(C)C>C(Cl)Cl>[NH2:15][C:16]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]2[C:17]=1[CH:18]=[CH:19][N:20]2[C:26]([C:33]1[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=1)([CH2:31][CH3:32])[C:27]([O:29][CH3:30])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70562026HCID 70562026, compound

Product 1

HCID 70562875HCID 70562875, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4 mL) was added rapidly dropwise to a stirred solution of methyl 2-(4-(tert-butoxycarbonylamino)-6-fluoro-1H-indol-1-yl)-2-(4-chlorophenyl)butanoate (0.92 g, 2 mmol) in DCM (10 mL) at 0° C. After 1 h, the reaction was quenched by careful addition of saturated aqueous sodium bicarbonate, followed by extraction with ether. The organic layers were washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound. LC/MS m/z=361.1 [M+H]+.

Workup

  1. customthe reaction was quenched by careful addition of saturated aqueous sodium bicarbonate
  2. extractionfollowed by extraction with ether
  3. washThe organic layers were washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f0194c8c7e94301b08ddaee92ea12cb
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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