Ethyl chloroformate → 2-Carboethoxyamino-3-carboethoxy-6-acetyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 1935459Notes

Reaction equation

HRID 1935459 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].C(=O)([O-])[O-].[K+].[K+].[NH2:13][C:14]1[S:25][C:17]2[CH2:18][N:19]([C:22](=[O:24])[CH3:23])[CH2:20][CH2:21][C:16]=2[C:15]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]>C1(C)C=CC=CC=1>[C:2]([NH:13][C:14]1[S:25][C:17]2[CH2:18][N:19]([C:22](=[O:24])[CH3:23])[CH2:20][CH2:21][C:16]=2[C:15]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])([O:4][CH2:5][CH3:6])=[O:3]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 212358Thieno(2,3-c)pyridine-3-carboxylic acid, 4,5,6,7-tetrahydro-6-acetyl-6-amino-, ethyl ester

Product 1

HCID 224646792-Carboethoxyamino-3-carboethoxy-6-acetyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridineYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.0 g (28 mmol) of ethyl chloroformate and 2.6 g (18.6 mmol) of finely powdered potassium carbonate were added to 5.0 g (18.6 mmol) of 2-amino-3-carboethoxy-6-acetyl-4,5,6,7-tetrahydrothieno-[2,3-c]pyridine in 50 ml of toluene and the mixture was boiled at reflux for 2 h. After that, the reaction mixture was taken up in ice/water, after which the toluene phase was separated off and the aqueous phase was reextracted with toluene. After drying, the combined organic phases were evaporated. 5.8 g (92%) of product were isolated as an oil, which slowly crystallizes to some degree.

Workup

  1. temperatureat reflux for 2 h
  2. customafter which the toluene phase was separated off
  3. customAfter drying
  4. customthe combined organic phases were evaporated

Sources & evidence

ORD record
ord-e030baa870c049849a6b0f88ad371f09
Source dataset
uspto-grants-2002_05
Patent number
US06387912B1

Reaction notes

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