Ethyl Acetate → HCID 21939926, compound

HRID 1242915Notes

Reaction equation

HRID 1242915 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][C:17]3[CH:37]=[CH:36][C:20]([C:21]([CH:23]4[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]4)=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].C(OCC)(=O)C>CO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:16][C:17]3[CH:37]=[CH:36][C:20]([CH:21]([OH:22])[CH:23]4[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[CH2:24]4)=[CH:19][CH:18]=3)=[O:15])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 21939751HCID 21939751, compound

Product 1

HCID 21939926HCID 21939926, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 3-[4-[[(4′-chloro[1,1′-biphenyl]-4-yl)carbonyl]amino]benzoyl]-1-piperidinecarboxylate (506 mg, 0.975 mmol) obtained in Example 127-1) was dissolved in a mixed solution of methanol and tetrahydrofuran (1:1) (10 ml). Sodium borohydride (73.8 mg, 1.95 mmol) was added to the solution under ice-cooling, which was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. Diisopropyl ether was added to the residue, to give the titled compound (488 mg) as a colorless powder.

Workup

  1. temperaturecooling
  2. washwas washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled out under reduced pressure
  5. additionDiisopropyl ether was added to the residue

Sources & evidence

ORD record
ord-b375baacac6c41af867bd09f940bfbed
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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