Hydrochloric Acid → HCID 19063100, compound

HRID 482486Notes

Reaction equation

HRID 482486 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([C:22](=[O:32])[CH2:23][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:18][CH2:17]2)[N:3]=1.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO.O.CC(C)=O>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([C:22](=[O:32])[CH2:23][CH:24]([OH:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:18][CH2:17]2)[N:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride2×HCID 9867616HCID 9867616, compound

Product 1

HCID 19063100HCID 19063100, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 3 g of the compound prepared in Example 13 in 50 ml MeOH a solution of 0.43 g of NaBH4 96% in 4 ml iced H2O containing 0.2 ml NaOH 30% is quickly added and the mixture is stirred at room temperature for 8 h. Thereafter 2 g (5×0.4) of NaBH4 are added in 8 h. The suspension is diluted with 10 ml acetone, treated with diluted HCl, neutralized with sodium bicarbonate in 5% solution and concentrated under vacuum. The aqueous suspension is diluted with H2O and extracted with CHCl3 ; the organic phase is washed with H2O, dried on anhydrous Na2SO4 and the residue, obtained by evaporation of the solvent, is purified by flash chromatography on SiO2 column eluting with CH2Cl2 /MeOH 100:5. The crude compound, obtained after pooling the pure fractions and evaporating the solvent, is crystallized from EtOH giving 2.34 g (79%) of the wanted compound; m.p.: 222° C.

Workup

  1. additionis quickly added
  2. concentrationconcentrated under vacuum
  3. additionThe aqueous suspension is diluted with H2O
  4. extractionextracted with CHCl3
  5. washthe organic phase is washed with H2O
  6. dry with materialdried on anhydrous Na2SO4
  7. customthe residue, obtained by evaporation of the solvent
  8. customis purified by flash chromatography on SiO2 column
  9. washeluting with CH2Cl2 /MeOH 100:5

Sources & evidence

ORD record
ord-cff1816f02d6474a9e584bbd2b967d30
Source dataset
uspto-grants-1998_08
Patent number
US05798362

Reaction notes

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