Reaction #75406

ord-43806bf1c4eb4b53b1e20147dc65efec

Reaction equation

CC(=O)SCC(CSC(C)=O)C(=O)N1CCC[C@H]1C(=O)O
(2-Acetylthiomethyl-3-(acetylthio)propanoyl]-L-proline
Cl
hydrochloric acid
→
O=C(O)[C@@H]1CCCN1C(=O)C(CS)CS
1-(2-Mercaptomethyl-3-mercaptopropanoyl)-L-proline

Reactants

CC(=O)SCC(CSC(C)=O)C(=O)N1CCC[C@H]1C(=O)O
(2-Acetylthiomethyl-3-(acetylthio)propanoyl]-L-proline
Cl
hydrochloric acid

Reagents

None

Solvents

O
water
N
ammonia

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.WAITAfter twenty minutes
  2. 2
    FiltrationThe crystalline precipitate 1-(2-mercaptomethyl-3-mercaptopropanoyl)-L-proline is filtered
  3. 3
    Otherdried

Procedure

1-[(2-Acetylthiomethyl-3-(acetylthio)propanoyl]-L-proline (1.2 g.) is dissolved in a mixture of water (12 ml.) and concentrated ammonia (12 ml.) under an atmosphere of argon. After twenty minutes, the mixture is acidified with concentrated hydrochloric acid. The crystalline precipitate 1-(2-mercaptomethyl-3-mercaptopropanoyl)-L-proline is filtered and dried, yield 0.63 g., m.p. 138°-140°.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04176235uspto-grants-1979_11