Acetic Acid → HCID 13922882, compound

HRID 2232362Notes

Reaction equation

HRID 2232362 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH:11]=[C:10]([S:12](=[O:15])(=[O:14])[NH2:13])[S:9][C:8]=2[CH:16]=1)(=[O:3])[CH3:2].[BH4-].[Na+].[NH4+].[Cl-].C(O)(=O)C>CO.[OH-].[Na+]>[OH:3][CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH:11]=[C:10]([S:12](=[O:14])(=[O:15])[NH2:13])[S:9][C:8]=2[CH:16]=1)[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 13922881HCID 13922881, compound

Product 1

HCID 13922882HCID 13922882, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

The acetyl compound from Example 38 (1.79 g, 7 mmole) was dissolved in 40 ml of CH3OH, cooled to 0° C. and NaBH4 (264 mg, 7 mmole) in 4 ml of 40% NaOH was added. The reaction mixture was stirred for 25 minutes then 2.5 g of NH4Cl was added followed by 1 ml glacial acetic acid. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (75 ml) and 20% saturated NaHCO3 (50 ml). The ethyl acetate layer was washed with H2O (50 ml) and the combined aqueous solution was back-extracted with ethyl acetate. The ethyl acetate extracts were combined and dried over Na2SO4. The solvent was removed in vacuo and the residue was crystallized from CHCl3 -dichloroethane yielding 1.56 g (86.7%) of product, m.p. 134°-35° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (75 ml) and 20% saturated NaHCO3 (50 ml)
  3. washThe ethyl acetate layer was washed with H2O (50 ml)
  4. extractionthe combined aqueous solution was back-extracted with ethyl acetate
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed in vacuo
  7. customthe residue was crystallized from CHCl3 -dichloroethane yielding 1.56 g (86.7%) of product, m.p. 134°-35° C.

Sources & evidence

ORD record
ord-2218b6160e9b482580490dfe8b6649e9
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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