Ethyl chloroformate → HCID 15053404, compound

HRID 1032181Notes

Reaction equation

HRID 1032181 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[O:12])[CH2:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>O1CCCC1.O>[CH2:31]([O:30][C:28]([N:16]1[CH2:17][CH2:18][N:13]([C:11]([N:9]2[CH2:8][CH:7]([O:6][C:5]3[CH:19]=[CH:20][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:10]2)=[O:12])[CH2:14][CH2:15]1)=[O:29])[CH3:32]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 15053406HCID 15053406, compound

Product 1

HCID 15053404HCID 15053404, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 2.8 g (0.01 mole) of 1-[3-(4-fluorophenoxy)-1-azetidinylcarbonyl]piperazine and 1.4 g (0.01 mole) of potassium carbonate in 20 ml of tetrahydrofuran was treated with 1.1 g (0.01 mole) of ethyl chloroformate. After stirring for 15 minutes, a small piece of ice was added and stirring continued for 72 hr. The reaction mixture was diluted with water and the oil which separated solidified on standing. The solid residue was purified by column chromatography (silica gel; washed with chloroform and eluted with ethyl acetate) to give the product 2.5 g (71%) which was recrystallized from benzene/ligroin to yield 2.35 g (66.7%) of white crystalline product, m.p. 89°-90° C.

Workup

  1. additiona small piece of ice was added
  2. stirringstirring
  3. waitcontinued for 72 hr
  4. customthe oil which separated
  5. customThe solid residue was purified by column chromatography (silica gel; washed with chloroform and eluted with ethyl acetate)

Sources & evidence

ORD record
ord-daf4e8a1930445cdaadb0802e9d3b296
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

Loading…