Hydrochloric Acid → HCID 67585366, compound

HRID 727640Notes

Reaction equation

HRID 727640 reaction equation
[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([C:27]([NH:29][C@H:30]3[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31]3)=[O:28])[CH2:10]2)=[CH:5][CH:4]=1.[ClH:44]>C(OCC)(=O)C>[ClH:44].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=3)=[O:15])[C@H:11]([C:27]([NH:29][C@H:30]3[CH2:34][CH2:33][NH:32][CH2:31]3)=[O:28])[CH2:10]2)=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67585136HCID 67585136, compound

Product 1

HCID 67585366HCID 67585366, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 1.00 g of (2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-1-(t-butoxycarbonyl)pyrrolidin-3-ylaminocarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (i) above] and 10 ml of ethyl acetate was heated to form a solution. 2.5 ml of a 4N solution of hydrogen chloride in ethyl acetate were then added to this solution, and the resulting mixture was heated under reflux for 30 minutes. At the end of this time, the solvent was removed by distillation under reduced pressure, and then, in order to remove the acid, ethyl acetate was added to the residue and the solvent was again removed by distillation under reduced pressure. The residue was triturated with diethyl ether and washed by decantation to give 630 mg of the title compound, as a powder.

Workup

  1. temperaturewas heated
  2. customto form a solution
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for 30 minutes
  5. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  6. customin order to remove the acid, ethyl acetate
  7. additionwas added to the residue
  8. customthe solvent was again removed by distillation under reduced pressure
  9. customThe residue was triturated with diethyl ether
  10. washwashed by decantation

Sources & evidence

ORD record
ord-3f303294103c426fbf6b8c485da13f5e
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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