Trifluoroacetic acid → Trifluoroacetate

HRID 977216Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH:13]([C:15]([NH:17][C@H:18]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:19]([O:21]C(C)(C)C)=[O:20])=[O:16])[O:12][C:11]2=[O:33])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:14][CH:13]([C:15]([NH:17][C@H:18]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:19]([OH:21])=[O:20])=[O:16])[O:12][C:11]2=[O:33])=[CH:8][CH:9]=1)(=[NH:2])[NH2:3].[F:34][C:35]([F:40])([F:39])[C:36]([O-:38])=[O:37]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 70098694HCID 70098694, compound

Product 2

HCID 84468Trifluoroacetate

HCID 70099942HCID 70099942, compound

Procedure

0.25 g of tert-butyl (2R)-2-[3-(4-amidinophenyl)-2-oxo-5-oxazolidinylcarbonylamino)-3phenylpropionate [obtainable according to Example 12]is stirred in 10 ml of trifluoroacetic acid at room temperature until hydrolysis is complete. The reaction mixture is subsequently concentrated and the residue is washed repeatedly with toluene. Treatment with ethyl acetate gives (2R)-2-[3-(4-amidinophenyl)-2-oxo-5-oxazolidinylcarbonylamino]-3-phenylpropionic acid, trifluoroacetate, FAB (M+1): 397.

Workup

concentrationThe reaction mixture is subsequently concentrated
washthe residue is washed repeatedly with toluene

Sources & evidence

ORD record: ord-3e68cd002b9a4163bb148e5b9b72231b
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05614535

Reaction notes

Loading…