Acetic Acid → [4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-2-(dimethylamino)-1,1'-biphenyl-4-yl]acetic acid

HRID 2076649Notes

Reaction equation

HRID 2076649 reaction equation
C=O.[C:3](O)(=O)C.[BH4-].[C:8]([Na])#[N:9].N[C:12]1[CH:17]=[C:16]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:14][C:13]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[C:32]([OH:40])[C:31]=2[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[CH:24][CH:23]=1>C(#N)C.O>[C:44]([O:43][C:41]([C:31]1[C:32]([OH:40])=[C:33]([C:36]([F:39])([F:37])[F:38])[CH:34]=[CH:35][C:30]=1[CH2:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:13]2[CH:14]=[CH:15][C:16]([CH2:18][C:19]([OH:21])=[O:20])=[CH:17][C:12]=2[N:9]([CH3:8])[CH3:3])=[CH:27][CH:26]=1)=[O:42])([CH3:46])([CH3:45])[CH3:47]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 11540867(2-Amino-4'-{[2-(tert-butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetic acidHCID 178511851HCID 178511851, compound

Product 1

HCID 67119210[4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-2-(dimethylamino)-1,1'-biphenyl-4-yl]acetic acidYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

36% aqueous formaline solution (0.5 ml), acetic acid (100 μl) and cyano sodium borohydride (36 mg, 0.59 mmol) were successively added to a solution of (2-amino-4′-{[2-(tert-butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-4-yl)acetic acid (50 mg, 0.096 mmol) obtained in Example 38 in acetonitrile (4 ml), and the mixture was stirred at room temperature overnight. After the reaction mixture was poured into water and extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel preparative thin layer chromatography (developing solvent: methylene chloride/methanol=20/1) to give the title compound as a yellow oil (48 mg, yield: 92%.)

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customThe residue obtained
  5. customby removing the solvent under reduced pressure
  6. customwas purified by silica gel preparative thin layer chromatography (developing solvent: methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-194f0477f571462096827a0068ae633a
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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