Hydrochloric Acid → HCID 22011008, compound

HRID 323170Notes

Reaction equation

HRID 323170 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:38]=[CH:37][C:20]([C:21]([N:23]([CH2:31][C:32](OCC)=[O:33])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>C(O)C.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH2:31][CH2:32][OH:33])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])=[O:22])=[CH:37][CH:38]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride2×HCID 22010672HCID 22010672, compound

Product 1

HCID 22011008HCID 22011008, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-ethoxycarbonylmethyl-N-(2-methylphenyl)benzamide (100 mg) in ethanol (5 ml) was added sodium borohydride (37 mg) at 0° C. and the mixture was stirred for 2 hours at ambient temperature. Since the reaction was not completed and it was so slow, sodium borohydride (220 mg) was added to the mixture at 0° C. and stirred overnight. The reaction mixture was neutralized with 1N hydrochloric acid and diluted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. Filtering and the removal of solvents afforded 4-(4′-methylbiphenyl-2-carboxamido)-N-(2-hydroxyethyl)-N-(2-methylphenyl)benzamide (70 mg) as a colorless prisms.

Workup

  1. stirringstirred overnight
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltering
  5. customthe removal of solvents

Sources & evidence

ORD record
ord-3b67006252cb49ef84005d989d1e1616
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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