HCID 21070796, compound → HCID 21070679, compound

HRID 499746Notes

Reaction equation

HRID 499746 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][CH:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:34][CH2:33][CH2:32][C@H:24]4C(OC(C)(C)C)=O)=[CH:19][CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1>ClCCl.FC(F)(F)C(O)=O>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][CH:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:34][CH2:33][CH2:32][CH2:24]4)=[CH:19][CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 21070796HCID 21070796, compound

Product 1

HCID 21070679HCID 21070679, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

780 mg (1.54 mmol) of tert-butyl 1-{4-[5-({[(5-chloro-2-thienyl)carbonyl]amino}-methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}prolinate are dissolved in 6 ml of dichloromethane and 9 ml of trifluoroacetic acid, and the mixture is stirred at 40° C. for two days. The reaction mixture is then concentrated and stirred with ether and 2 N sodium hydroxide solution. The aqueous phase is concentrated and stirred with ether and 2 N hydrochloric acid. The organic phase from this extraction is dried over MgSO4, filtered and concentrated. The crude product is chromatographed on silica gel (CH2Cl2/EtOH/conc. aq. NH3 solution=100/1/0.1 to 20/1/0.1).

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. concentrationThe aqueous phase is concentrated
  3. stirringstirred with ether and 2 N hydrochloric acid
  4. extractionThe organic phase from this extraction
  5. dry with materialis dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is chromatographed on silica gel (CH2Cl2/EtOH/conc. aq. NH3 solution=100/1/0.1 to 20/1/0.1)

Sources & evidence

ORD record
ord-e75460ddb0f344ce8170d25bd600035c
Source dataset
uspto-grants-2010_08
Patent number
US07767702B2

Reaction notes

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