Acetyl chloride → HCID 13747426, compound

HRID 1587089Notes

Reaction equation

HRID 1587089 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([CH2:15][C:16]([NH:18][CH:19]([CH2:32][OH:33])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:17])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(N(CC)CC)C.[C:41](Cl)(=[O:43])[CH3:42]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([CH2:15][C:16]([NH:18][CH:19]([CH2:32][O:33][C:41](=[O:43])[CH3:42])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)=[O:17])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 13747418HCID 13747418, compound

Product 1

HCID 13747426HCID 13747426, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a solution of ethyl 2-ethoxy-4-[N-(α-hydroxymethyl-2-piperidino-benzyl)-aminocarbonylmethyl]-benzoate (0.227 g, 0.5 mmol) and absolute triethylamine (0.126 ml, 0.9 mmol) in absolute chloroform (3 ml), a solution of acetyl chloride (0.063 ml, 0.9 mmol) in absolute chloroform (1 ml) is added dropwise. After 4 days' stirring at ambient temperature the mixture is diluted with chloroform, washed with dilute aqueous sodium bicarbonate solution, the chloroform solution is dried and filtered and evaporated down in vacuo. The evaporation residue is purified by column chromatography on silica gel (chloroform/acetone=4/1).

Workup

  1. washwashed with dilute aqueous sodium bicarbonate solution
  2. dry with materialthe chloroform solution is dried
  3. filtrationfiltered
  4. customevaporated down in vacuo
  5. customThe evaporation residue is purified by column chromatography on silica gel (chloroform/acetone=4/1)

Sources & evidence

ORD record
ord-fe6b02f2eb1d456da8c8ec102cd37991
Source dataset
uspto-grants-1993_06
Patent number
US05216167

Reaction notes

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