Trifluoroacetic acid → HCID 86600476, compound

HRID 2105538Notes

Reaction equation

HRID 2105538 reaction equation
C([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:11][CH:10]([CH2:18][N:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[O:21])[C:9]1=[O:30])(C)(C)C.C(O)(C(F)(F)F)=O>C(O)=O>[CH2:23]([O:22][N:19]([CH2:18][CH:10]1[C:9](=[O:30])[N:8]([CH2:7][C:6]([OH:31])=[O:5])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:11]1)[CH:20]=[O:21])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86600477HCID 86600477, compound

Product 1

HCID 86600476HCID 86600476, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The {2-[(benzyloxy-formyl-amino)-methyl]-3-oxo-2,3-dihydro-benzo[1,4]thiazin-4-yl}-acetic acid tert-butyl ester obtained in the previous step is treated with TFA (2.4 mmol) in 12 mL of formic acid. The reaction is stirred at room temperature for 3 hours. The solvent is removed and the mixture is purified by column chromatography (hexane/EtOAc) yielding {2-[(benzyloxy-formyl-amino)-methyl]-3-oxo-2,3-dihydro-benzo[1,4]thiazin-4-yl}-acetic acid. Yield: 50%. MS: (ES+): 359.2 [M+1].

Workup

  1. customThe solvent is removed
  2. customthe mixture is purified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-faf49f96dd574f98bb94fdd4488bfad6
Source dataset
uspto-grants-2009_08
Patent number
US07579363B2

Reaction notes

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