Acetic Acid → HCID 18996349, compound

HRID 374898Notes

Reaction equation

HRID 374898 reaction equation
[CH:1]([C:3]1[CH:21]=[CH:20][C:6]2[O:7][C:8]([C:15]([O:17]CC)=[O:16])([C:10]([O:12]CC)=[O:11])[O:9][C:5]=2[CH:4]=1)=O.[NH2:22][CH2:23][CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)[OH:25].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+:50]>ClCCCl>[Cl:32][C:28]1[CH:27]=[C:26]([CH:24]([OH:25])[CH2:23][NH:22][CH2:1][C:3]2[CH:21]=[CH:20][C:6]3[O:7][C:8]([C:15]([O-:17])=[O:16])([C:10]([O-:12])=[O:11])[O:9][C:5]=3[CH:4]=2)[CH:31]=[CH:30][CH:29]=1.[Na+:50].[Na+:50]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 5049666Sodium triacetoxyborohydrideHCID 19973517HCID 19973517, compound

Product 1

HCID 18996349HCID 18996349, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

One equivalent of the above aldehyde, one equivalent of 2-amino-1-(3-chlorophenyl)ethanol, one equivalent of acetic acid, and 1.5 equivalents of sodium triacetoxyborohydride in 1,2-dichloroethane is stirred at room temperature for 1 hour. The solvent is evaporated in vacuo. The residue dissolved in 2.5N sodium hydroxide in ethyl alcohol, heated at reflux temperature for one hour, and evaporated in vacuo. The residue is passed through an ion exchange column to give the title compound.

Workup

  1. customThe solvent is evaporated in vacuo
  2. dissolutionThe residue dissolved in 2.5N sodium hydroxide in ethyl alcohol
  3. temperatureheated
  4. temperatureat reflux temperature for one hour
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-133b738f91f14cc79b5e3e2f7ecffe4b
Source dataset
uspto-grants-1996_01
Patent number
US05482971

Reaction notes

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