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

HRID 325073Notes

Reaction equation

HRID 325073 reaction equation
[NH2:1][C:2]1[S:13][C:5]2[CH2:6][N:7]([C:10](=[O:12])[CH3:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[C:20]([NH:1][C:2]1[S:13][C:5]2[CH2:6][N:7]([C:10](=[O:12])[CH3:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])([O:22][CH2:23][CH3:24])=[O:21]

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

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 were mixed with 3.0 g (28 mmol) of ethyl chloroformate and 2.6 g (18.6 mmol) of finely powdered potassium carbonate and refluxed for 2 h. The reaction mixture was then taken up in ice/water, the toluene phase was separated off, and the aqueous phase was back-extracted with toluene. The combined organic phases were dried and then concentrated. 5.8 g (92%) of product were isolated as an oil which slowly crystallizes somewhat.

Workup

  1. temperaturerefluxed for 2 h
  2. customthe toluene phase was separated off
  3. extractionthe aqueous phase was back-extracted with toluene
  4. customThe combined organic phases were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b65b536d7f6428bbc3ef693580305ac
Source dataset
uspto-grants-2001_04
Patent number
US06222034B1

Reaction notes

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