HCID 86760906, compound → HCID 86760905, compound

HRID 1988279Notes

Reaction equation

HRID 1988279 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:19][C:20](=[O:46])[CH:21]([N:25]([C:27](=[O:45])[CH:28]([NH:37]C(OCCCC)=O)[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[CH3:26])[CH:22]([CH3:24])[CH3:23])[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:19][C:20](=[O:46])[CH:21]([N:25]([C:27](=[O:45])[CH:28]([NH2:37])[CH2:29][C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)[CH3:26])[CH:22]([CH3:24])[CH3:23])[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 86760906HCID 86760906, compound

Product 1

HCID 86760905HCID 86760905, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-((2-butoxycarbonylamino-3-(4-fluorophenyl)propionyl)-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide (B) (1.48 g, 2.26 mmol) in methylene chloride (20 ml), TFA (10 ml) was added and stirred at room temperature for 1.5 hours. The reaction mixture was evaporated to remove the solvent under reduced pressure; the thus obtained residue was mixed with methylene chloride, washed with a 2N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure. The thus obtained residue was subjected to silica gel column chromatography (developing solvent: methanol:aqueous ammonia:methylene chloride=3:0.1:100), giving the titled compound (587 mg).

Workup

  1. customThe reaction mixture was evaporated
  2. customto remove the solvent under reduced pressure
  3. additionthe thus obtained residue was mixed with methylene chloride
  4. washwashed with a 2N aqueous sodium hydroxide solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-2e2b7aa451e14ae3867e2752654e899d
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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