Trifluoroacetic acid → HCID 11333230, compound

HRID 1253875Notes

Reaction equation

HRID 1253875 reaction equation
C(OC(N(CC(O)=O)C[C:13]1[CH:18]=[C:17](F)[C:16](F)=[CH:15][C:14]=1[NH:21]C(OC(C)(C)C)=O)=O)C1C=CC=CC=1.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>C(Cl)Cl>[F:33][C:34]([F:39])([F:38])[C:35]([O-:37])=[O:36].[C:14]1([NH3+:21])[CH:15]=[CH:16][CH:17]=[CH:18][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68628330HCID 68628330, compound

Product 1

HCID 11333230HCID 11333230, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {benzyloxy carbonyl-(2-tert-butoxycarbonylamino-4,5-difluoro-benzyl)-amino]-acetic acid} (4.76 g, 10.56 mmol) in dry DCM (40 mL) was added trifluoroacetic acid (14.35 mL, 3 mL/mmol) at 0° C. The reaction mixture was stirred at r.t. for 2 h under argon. After completion of the reaction as confirmed by TLC, the reaction mixture was evaporated in vacuo to remove excess of solvent and trifluoroacetic acid. The remaining were removed under vacuo and 2-[(benzyloxycarbonyl-carboxymethyl-amino)-methyl]-4,5-difluoro, phenyl-ammonium trifluoroacetate (4.75 g, 97%) was obtained as thick brown jelly which was used as such without any further purification for the next step.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was evaporated in vacuo
  3. customto remove excess of solvent and trifluoroacetic acid
  4. customThe remaining were removed under vacuo and 2-[(benzyloxycarbonyl-carboxymethyl-amino)-methyl]-4,5-difluoro

Sources & evidence

ORD record
ord-1053585601594972b4dc0839fa311ea9
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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