1-Hydroxybenzotriazole → 1-[(2-Benzothienylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl ester

HRID 1851833Notes

Reaction equation

HRID 1851833 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]=[C:14]1[C:22]([OH:24])=O.[C:25]1([CH2:31][O:32][C:33]([C:35]2([NH2:41])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[O:34])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[C:25]1([CH2:31][O:32][C:33]([C:35]2([NH:41][C:22]([C:14]3[S:13][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[CH:15]=3)=[O:24])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]2)=[O:34])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 95864Benzo(b)thiophene-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15176238Benzyl 1-aminocyclohexanecarboxylate

Product 1

HCID 576728971-[(2-Benzothienylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, 5.9 g (31 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 5 g (28 mmol) of 2-benzothiophenecarboxylic acid, 6.5 g (28 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester and 4.5 g (29 mmol) of 1-hydroxybenzotriazole in methylenechloride. After the mixture was stirred at room temperature overnight, the reaction solvent was distilled off under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate twice. The obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution, and then saturated brine, followed by drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and diethyl ether was added to the obtained residue, followed by stirring of the mixture overnight. The crystal was collected by filtration and was heated and dried under reduced pressure to obtain 10 g (91%) of the title compound.

Workup

  1. temperatureUnder ice-cooling
  2. distillationthe reaction solvent was distilled off under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate twice
  5. washThe obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution
  6. dry with materialby drying with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure, and diethyl ether
  8. additionwas added to the obtained residue
  9. stirringby stirring of the mixture overnight
  10. filtrationThe crystal was collected by filtration
  11. temperaturewas heated
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-bf7d56e0af0a4f29ac4fe01e2bccb444
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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