HCID 135665582, compound → HCID 135665583, compound

HRID 1988261Notes

Reaction equation

HRID 1988261 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 91.8%

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 (B) (93 mg) in methylene chloride (5 ml), TFA (1 ml) was added under cooling with ice. The resultant mixture was stirred at room temperature for 1.5 hours and evaporated under reduced pressure to remove the solvent; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: methylene chloride:methanol=15:1), giving the titled compound (70 mg, 91.8%).

Workup

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

Sources & evidence

ORD record
ord-f889251650b249a5a2c34faedd7605b2
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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