Ethyl chloroformate → HCID 15053404, compound

HRID 974651Notes

Reaction equation

HRID 974651 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-fd87e545347b425bb11850e68a21de5e
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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