HCID 135665582, compound → HCID 135665583, compound

HRID 1988260Notes

Reaction equation

HRID 1988260 reaction equation
C(OC([NH:8][CH:9]([CH2:42][C:43]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=1)[C:10]([N:12]([CH:14]([CH:39]([CH3:41])[CH3:40])[C:15]([NH:17][CH:18]([C:31]1[NH:36][C:35](=[O:37])[CH:34]=[C:33]([CH3:38])[N:32]=1)[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:21]=1)=[O:16])[CH3:13])=[O:11])=O)CCC>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:8][CH:9]([CH2:42][C:43]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=1)[C:10]([N:12]([CH:14]([CH:39]([CH3:41])[CH3:40])[C:15]([NH:17][CH:18]([C:31]1[NH:36][C:35](=[O:37])[CH:34]=[C:33]([CH3:38])[N:32]=1)[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:21]=1)=[O:16])[CH3:13])=[O:11]

Participants

4

Reactant 1

HCID 135665582HCID 135665582, compound

Product 1

HCID 135665583HCID 135665583, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-(1-(2-((2-butoxycarbonylamino-3-(4-fluorophenyl)propionyl)-N-methylamino)-3-methyl-butyrylamino)-2-(3-tert-butyl-4-hydroxyphenyl)ethyl)-6-methyl-4-pyrimidinone (A) (279 mg) in methylene chloride (8 ml), TFA (1.3 ml) was added under cooling with ice. The resultant mixture was stirred at room temperature for 1 hour and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: methylene chloride:methanol=15:1), giving the titled compound (225 mg, 95%).

Workup

  1. temperatureunder cooling with ice
  2. customevaporated
  3. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-1074a599d15c401e8b5e0a01539ea27e
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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