Trifluoroacetic acid → HCID 58951420, compound

HRID 1445748Notes

Reaction equation

HRID 1445748 reaction equation
C(O[C:6](=O)[N:7]([CH:9]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])[CH2:10]1)C)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([C:18]2[O:19][C:20]([CH3:21])=[C:16]([CH2:15][CH2:14][N:11]3[CH2:12][CH2:13][CH:9]([NH:7][CH3:6])[CH2:10]3)[N:17]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58951455HCID 58951455, compound2×

Product 1

HCID 58951420HCID 58951420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir (1-{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-pyrrolidin-3-yl)-methyl-carbamic acid tert-butyl ester (see Intermediate 10) with a 1:1 solution of trifluoroacetic acid and dichloromethane (0.30M) for 30 minutes at room temperature. After this time, quench the reaction with 1N sodium hydroxide and extract with dichloromethane. Extract from the organic layer with 1N hydrochloric acid. Basify the aqueous layer with 1N sodium hydroxide and extract with dichloromethane. Dry the organics with sodium sulfate, decant and concentrate in vacuo to yield the pure title compound, MS (m/e) (79Br/81Br): 364.1/366.0 (M+1)

Workup

  1. customAfter this time, quench
  2. customthe reaction with 1N sodium hydroxide
  3. extractionextract with dichloromethane
  4. extractionExtract from the organic layer with 1N hydrochloric acid
  5. extractionextract with dichloromethane
  6. dry with materialDry the organics with sodium sulfate
  7. customdecant
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-07a97fcd46c64353af60a7524b08ffeb
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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