Hydrochloric Acid → 2-[(3R)-3-carbamoyloxypyrrolidin-1-yl]-2-iminoethylmercaptan hydrochloride

HRID 622411Notes

Reaction equation

HRID 622411 reaction equation
P(=[S:5])([O-])([O-])[O-].[Na+].[Na+].[Na+].Cl.[C:10]([O:13][C@@H:14]1[CH2:18][CH2:17][N:16]([C:19](=[NH:22])[CH2:20][Cl:21])[CH2:15]1)(=[O:12])[NH2:11].Cl>O>[ClH:21].[C:10]([O:13][C@@H:14]1[CH2:18][CH2:17][N:16]([C:19](=[NH:22])[CH2:20][SH:5])[CH2:15]1)(=[O:12])[NH2:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9877537Trisodium thiophosphateHCID 679383042-[(3R)-3-carbamoyloxypyrrolidin-1-yl]-2-iminoethylchloride hydrochloride

Product 1

HCID 867424262-[(3R)-3-carbamoyloxypyrrolidin-1-yl]-2-iminoethylmercaptan hydrochlorideYield 104.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.945 g of trisodium phosphorothioate were added to a solution of 1.21 g of 2-[(3R)-3-carbamoyloxypyrrolidin-1-yl]-2-iminoethylchloride hydrochloride in 8 ml of water, kept cooled in ice-water, and the mixture was stirred for about 3 hours at room temperature. After adding 6 ml of 1N hydrochloric acid, the mixture was heated to 50° C. for 30 minutes, and the solvent was then distilled off under reduced pressure. The concentrate was mixed with 8 ml of methanol, insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was crystallized by adding ether, and the crystals were collected by filtration and washed with ether, giving 1.25 g of 2-[(3R)-3-carbamoyloxypyrrolidin-1-yl]-2-iminoethylmercaptan hydrochloride.

Workup

  1. temperaturethe mixture was heated to 50° C. for 30 minutes
  2. distillationthe solvent was then distilled off under reduced pressure
  3. additionThe concentrate was mixed with 8 ml of methanol, insolubles
  4. filtrationwere filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe concentrate was crystallized
  7. additionby adding ether
  8. filtrationthe crystals were collected by filtration
  9. washwashed with ether

Sources & evidence

ORD record
ord-b5740fd6bed84aeb992dc42e98744157
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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