Hydrochloric Acid → 1-[2-(acetylthiomethyl)-5-hydroxy-6-methylheptanoyl]-L-proline

HRID 262722Notes

Reaction equation

HRID 262722 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:17][CH2:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])(=[O:3])[CH3:2].[BH4-].[Na+].Cl>CO.O>[C:1]([S:4][CH2:5][CH:6]([CH2:17][CH2:18][CH:19]([OH:23])[CH:20]([CH3:21])[CH3:22])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 542745461-{2-[(Acetylsulfanyl)methyl]-6-methyl-5-oxoheptanoyl}-L-proline

Product 1

HCID 543289601-[2-(acetylthiomethyl)-5-hydroxy-6-methylheptanoyl]-L-proline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-[2-(acetylthiomethyl)-5-oxo-6-methylheptanoyl]-L-proline (1.5 g.) is dissolved in cold methanol (10 ml.) and sodium borohydride (0.12 g.) is added. After two hours the reaction mixture is diluted with water (100 ml.) acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer is dried and concentrated to dryness in vacuo to give 1-[2-(acetylthiomethyl)-5-hydroxy-6-methylheptanoyl]-L-proline.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer is dried
  3. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-5aeda20ec24945c88e2a78a4c400de3c
Source dataset
uspto-grants-1979_05
Patent number
US04154936

Reaction notes

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