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

HRID 1391098Notes

Reaction equation

HRID 1391098 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-ca2647e4b6574032bcaec887f3f7085f
Source dataset
uspto-grants-1979_02
Patent number
US04140864

Reaction notes

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