Hydrochloric Acid → HCID 19908457, compound

HRID 1534874Notes

Reaction equation

HRID 1534874 reaction equation
[BH4-].[Na+].[CH2:3]([CH:6]1[S:11][C:10]2[S:12][C:13]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:14][C:9]=2[C:8](=[O:19])[CH2:7]1)[CH2:4][CH3:5].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[OH:19][CH:8]1[CH2:7][CH:6]([CH2:3][CH2:4][CH3:5])[S:11][C:10]2[S:12][C:13]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:14][C:9]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 67917930HCID 67917930, compound

Product 1

HCID 19908457HCID 19908457, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (9.46 g, 0.25 mol) was added over 10 minutes to a stirred suspension of 4 (56.0 g, 0.19 mol) in absolute ethanol (1900 ml) under nitrogen. The mixture was refluxed for 2 hours and stirred at ambient temperature for 20 hours. After acidification with 1N hydrochloric acid (270 ml), followed by addition of saturated sodium bicarbonate solution (200 ml), the mixture was concentrated in vacuo. The residue was distributed between ethyl acetate (1000 ml) and water (600 ml), the aqueous layer was separated and extracted with ethyl acetate (2×600 ml), the combined ethyl acetate extracts were washed with saturated sodium bicarbonate, twice with water and dried over sodium sulfate. Evaporation in vacuo afforded 55.73 g (99%) of homogeneous product.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. concentrationthe mixture was concentrated in vacuo
  3. customthe aqueous layer was separated
  4. extractionextracted with ethyl acetate (2×600 ml)
  5. washthe combined ethyl acetate extracts were washed with saturated sodium bicarbonate, twice with water
  6. dry with materialdried over sodium sulfate
  7. customEvaporation in vacuo

Sources & evidence

ORD record
ord-4e3363a735114e8d938b3dac8c114112
Source dataset
uspto-grants-1992_02
Patent number
US05091409

Reaction notes

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