Trifluoroacetic acid → n[((5s)-3-{4-[(3r)-3-Amino-2-oxo-1-pyrrolidinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]-5-chloro-2-thiophenecarboxamide trifluoroacetate

HRID 41094Notes

Reaction equation

HRID 41094 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@@H:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:27][CH2:26][C@@H:25]([NH:28]C(=O)OC(C)(C)C)[C:24]4=[O:36])=[CH:19][CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>C(Cl)Cl>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[NH2:28][C@@H:25]1[CH2:26][CH2:27][N:23]([C:20]2[CH:21]=[CH:22][C:17]([N:13]3[CH2:12][C@H:11]([CH2:10][NH:9][C:7]([C:5]4[S:6][C:2]([Cl:1])=[CH:3][CH:4]=4)=[O:8])[O:15][C:14]3=[O:16])=[CH:18][CH:19]=2)[C:24]1=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57496678Tert-butyl (3r)-1-{4-[(5s)-5-({[(5-chloro-2-thienyl)carbonyl]amino}methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-2-oxo-3-pyrrolidinylcarbamate

Product 1

HCID 21070793n[((5s)-3-{4-[(3r)-3-Amino-2-oxo-1-pyrrolidinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]-5-chloro-2-thiophenecarboxamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

97 mg (0.181 mmol) of tert-butyl (3R)-1-{4-[(5S)-5-({[(5-chloro-2-thienyl)carbonyl]amino}methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-2-oxo-3-pyrrolidinylcarbamate are suspended in 4 ml of methylene chloride, 1.5 ml of trifluoroacetic acid are added and the mixture is stirred at room temperature for 1 hour. The mixture is then concentrated under reduced pressure and the residue is purified on an RP-HPLC (acetonitrile/water/0.1% TFA gradient). Evaporation of the appropriate fraction gives 29 mg (37% of theory) of the target compound of melting point 241° C. (decomp.).

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. customthe residue is purified on an RP-HPLC (acetonitrile/water/0.1% TFA gradient)
  3. customEvaporation of the appropriate fraction
  4. customgives 29 mg (37% of theory) of the target compound of melting point 241° C. (decomp.)

Sources & evidence

ORD record
ord-3e33ad0a2b1b4cf28d9d8d8c08b90986
Source dataset
uspto-grants-2013_09
Patent number
US08530505B2

Reaction notes

Loading…