Sodium Hydroxide → (4S)-4-{[(4-Methoxyphenyl)methyl]sulfanyl}-L-proline

HRID 37336Notes

Reaction equation

HRID 37336 reaction equation
Cl.[C:2]([C@@H:5]1[CH2:9][C@H:8]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:7][NH:6]1)(=[O:4])N.[OH-:20].[Na+]>Cl>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][S:10][C@@H:8]2[CH2:7][NH:6][C@H:5]([C:2]([OH:20])=[O:4])[CH2:9]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67585336HCID 67585336, compound

Product 1

HCID 15297070(4S)-4-{[(4-Methoxyphenyl)methyl]sulfanyl}-L-proline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4.0 g of (2S,4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine hydrochloride were dissolved in 40 ml of 2N aqueous hydrochloric acid, and the resulting solution was stirred for 1.5 hours on an oil bath at 95°-100° C. At the end of this time, the solution was cooled to room temperature, and then about 40 ml of a 2N aqueous solution of sodium hydroxide were added to the solution, whilst stirring, to adjust its pH to a value of between 4 and 6. The crystals which separated were collected by filtration, washed with water and dried in the air, to yield 3.25 g of the title compound as crystals, melting at 198°-200° C.

Workup

  1. stirringwhilst stirring
  2. customThe crystals which separated
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customdried in the air

Sources & evidence

ORD record
ord-9a39424839b3497db8126e56814af6db
Source dataset
uspto-grants-1995_05
Patent number
US05420119

Reaction notes

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