Hydrochloric Acid → HCID 12773668, compound

HRID 848460Notes

Reaction equation

HRID 848460 reaction equation
[SH:1][CH2:2][CH:3]([CH3:18])[C:4]([N:6]1[CH2:13][C:12](OC)([O:14]C)[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5].Cl>CCOCC>[SH:1][CH2:2][CH:3]([CH3:18])[C:4]([N:6]1[CH2:13][C:12](=[O:14])[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12821147HCID 12821147, compound

Product 1

HCID 12773668HCID 12773668, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The (S)-1-(3-mercapto-2-methyl-1-oxopropyl)-4,4-dimethoxy-L-proline (0.4 g., 0.0014 mole) is added to 8 ml. of stirred N HCl through which argon had previously been passed for ten minutes. After a solution is obtained, the flask is stoppered under argon and kept overnight at room temperature. The following steps are also carried out under an atmosphere of argon to the extent possible. To the stirred solution there is added 20 ml. of methylene chloride and after saturating with sodium chloride the layers are separated. The aqueous phase is extracted with additional methylene chloride (3×15 ml.), the organic layers are combined, dried (MgSO4), and the solvents evaporated to give a foamy residue. Following trituration with ether (evaporation repeated), 0.26 g. of (S)-1-(3-mercapto-2-methyl-1-oxopropyl)-4-oxo-L-proline are obtained as an amorphous solid (hygroscopic).

Workup

  1. customAfter a solution is obtained
  2. additionTo the stirred solution there is added 20 ml
  3. concentrationof methylene chloride and after saturating with sodium chloride the layers
  4. customare separated
  5. extractionThe aqueous phase is extracted with additional methylene chloride (3×15 ml.)
  6. dry with materialdried (MgSO4)
  7. customthe solvents evaporated
  8. customto give a foamy residue

Sources & evidence

ORD record
ord-2be0db3caa0e4a6c95717d2325d88552
Source dataset
uspto-grants-1981_10
Patent number
US04296113

Reaction notes

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