Acetic Acid → HCID 21465883, compound

HRID 1940200Notes

Reaction equation

HRID 1940200 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][N:5]([CH2:12][CH:13]([C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[NH2:28])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[C:6](=[O:11])[C:7]([F:10])([F:9])[F:8].C(O)(=O)C.[CH:34](=O)[C:35]([CH3:38])([CH3:37])[CH3:36].C([BH3-])#N.[Na+]>CO.ClCCl>[CH3:1][O:2][C:3](=[O:29])[CH2:4][N:5]([CH2:12][CH:13]([C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[NH:28][CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[C:6](=[O:11])[C:7]([F:10])([F:9])[F:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 12417PivalaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21465898HCID 21465898, compound

Product 1

HCID 21465883HCID 21465883, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[2-(2-amino-5-chlorophenyl)-2-(2-chlorophenyl)ethyl]-N-(trifluoroacetyl)glycine methyl ester (0.39 g) in methanol (5 ml) were added acetic acid (0.05 ml) and pivalaldehyde (78 mg). The mixture was stirred for 30 minutes at room temperature, to which was added sodium cyanoborohydride (57 mg). The mixture was stirred for one hour at room temperature, followed by addition of dichloromethane (50 ml) thereto. This solution was washed with a 1N aqueous solution of sodium hydroxide, then with water, followed by distilling off the solvent. The residue was purified by means of a silica-gel column chromatography (hexane:acetic acid ethyl ester=5:1 v/v as an eluent) to give 0.27 g of an oily compound.

Workup

  1. stirringThe mixture was stirred for one hour at room temperature
  2. washThis solution was washed with a 1N aqueous solution of sodium hydroxide
  3. distillationby distilling off the solvent
  4. customThe residue was purified by means of a silica-gel column chromatography (hexane

Sources & evidence

ORD record
ord-acce88be77b54cb3bbb441ee31e4e634
Source dataset
uspto-grants-1997_12
Patent number
US05698691

Reaction notes

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