Acetic Acid → HCID 135710754, compound

HRID 1755672Notes

Reaction equation

HRID 1755672 reaction equation
[NH2:1][CH:2]([CH3:29])[C:3]([NH:5][C:6]1[S:19][C:9]2[CH2:10][N:11]([C:14]([CH:16]3[CH2:18][CH2:17]3)=[O:15])[CH2:12][CH2:13][C:8]=2[C:7]=1[C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])=[O:4].C(O)(=O)C>C1(C)C=CC=CC=1.N1C=CC=CC=1>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]1[C:7]2[C:8]3[CH2:13][CH2:12][N:11]([C:14]([CH:16]4[CH2:18][CH2:17]4)=[O:15])[CH2:10][C:9]=3[S:19][C:6]=2[NH:5][C:3](=[O:4])[CH:2]([CH3:29])[N:1]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 14994971HCID 14994971, compound

Product 1

HCID 135710754HCID 135710754, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

12.95 g of 2-(2-aminopropionylamino)-3-(2-chlorobenzoyl)-6-cyclopropanecarbonyl-4,5,6,7-tetrahydro-thieno[2,3-C]pyridine was dissolved in 260 ml of toluene and 90 ml of pyridine, to which 5.4 g of acetic acid was added, followed by heating under reflux for 5 hours. After removal of the solvent by distillation, benzene was added and the resultant crystals were collected by filtration to obtain 2.96 g of the intended compound. The mother liquor was subjected to silica gel column chromatography (elution solvent: ethyl acetate:hexane=4:6) to obtain 3.84 g of the intended compound.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. customAfter removal of the solvent
  4. distillationby distillation, benzene
  5. additionwas added
  6. filtrationthe resultant crystals were collected by filtration

Sources & evidence

ORD record
ord-ee8776d0e89c4652b47ce4bdd27382e2
Source dataset
uspto-grants-1995_08
Patent number
US05438045

Reaction notes

Loading…