Trifluoroacetic acid → HCID 22039823, compound

HRID 1016748Notes

Reaction equation

HRID 1016748 reaction equation
C(OC([NH:8][C:9](=[NH:34])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][CH:17]([C:21]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=2[O:29][CH2:30][C:31]([OH:33])=[O:32])[C:18]([OH:20])=[O:19])=[CH:12][CH:11]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:9]([C:10]1[CH:11]=[CH:12][C:13]([NH:16][CH:17]([C:21]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=2[O:29][CH2:30][C:31]([OH:33])=[O:32])[C:18]([OH:20])=[O:19])=[CH:14][CH:15]=1)(=[NH:8])[NH2:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 145812992HCID 145812992, compound

Product 1

HCID 22039823HCID 22039823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

356 mg of (RS)-[4-(tert-butoxy carbonylamino-imino-methyl)-phenylamino]-(2-carboxymethoxy-5-methoxy-phenyl)-acetic acid were stirred in 3.7 ml of methylene chloride and 3.7 ml of TFA for one hour. The reaction mixture was evaporated in a vacuum and the residue was chromatographed on silica gel with ethyl acetate-acetone-water-acetic acid (6:2:1:1). From ethyl acetate-acetone-water-acetic acid (12:2:1:1) there was obtained crystalline (RS)-(4-carbamimidoyl-phenylamino)-(2-carboxymethoxy-5-methoxy-phenyl)-acetic acid, m.p. 213° C. MS: 374 (M+H)+.

Workup

  1. customThe reaction mixture was evaporated in a vacuum
  2. customthe residue was chromatographed on silica gel with ethyl acetate-acetone-water-acetic acid (6:2:1:1)

Sources & evidence

ORD record
ord-3f3dfe92bba940908d9badca8ec14b8b
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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