Trifluoroacetic acid → HCID 66679712, compound

HRID 1626766Notes

Reaction equation

HRID 1626766 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[C:8]12([C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([NH:28][C:29]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:30]=4[C:31]([O:33][CH3:34])=[O:32])=[O:27])=[CH:22][CH:21]=3)=O)[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.C([SiH](CC)CC)C>C(OCC)(=O)C>[C:8]12([CH2:18][C:20]3[CH:21]=[CH:22][C:23]([C:26]([NH:28][C:29]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:30]=4[C:31]([O:33][CH3:34])=[O:32])=[O:27])=[CH:24][CH:25]=3)[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][CH:14]([CH2:16]3)[CH2:15]1)[CH2:17]2.[C:8]12([CH:18]([O:2][C:1](=[O:7])[C:3]([F:6])([F:5])[F:4])[C:20]3[CH:21]=[CH:22][C:23]([C:26]([NH:28][C:29]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:30]=4[C:31]([O:33][CH3:34])=[O:32])=[O:27])=[CH:24][CH:25]=3)[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][CH:14]([CH2:16]3)[CH2:15]1)[CH2:17]2

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66680734HCID 66680734, compound

Product 2

HCID 66679712HCID 66679712, compoundYield 62%HCID 66680400HCID 66680400, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4 mL of TFA was added at room temperature to 350 mg (0.77 mmol) of methyl 2-({[4-(adamantan-1-ylcarbonyl)phenyl]carbonyl}amino)-5-chlorobenzoate obtained in Example 56-(ii). 360 mg (3.1 mmol) of triethyl silane was added thereto, and the mixture was stirred for 17 hours. The reaction mixture was diluted with ethyl acetate, and washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel chromatography, thereby giving 70 mg of methyl 2-({[4-(adamantan-1-ylmethyl)phenyl]carbonyl}amino)-5-chlorobenzoate (yield: 21%) and 262 mg of methyl 2-{[(4-{adamantan-1-yl[(trifluoro-acetyl)oxy]methyl]phenyl)carbonyl}amino}-5-chlorobenzoate (yield: 62%).

Workup

  1. washwashed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained crude product
  5. customwas separated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b0bdebea18cb4a08b5a50b0f09669589
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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