Ethyl Acetate → HCID 69217216, compound

HRID 2219294Notes

Reaction equation

HRID 2219294 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C@@:11]([CH3:18])([CH:13]([O:16][CH3:17])[O:14][CH3:15])[C@H:10]([OH:19])[C@@H:9]([N:20]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[CH2:21][C:22]3[N:23]=[N:24][N:25]([CH3:27])[N:26]=3)[C:8]=2[CH:35]=1)([O-])=O.[BH4-].[Na+].C(OCC)(=O)C>CO.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:12][C@@:11]([CH3:18])([CH:13]([O:14][CH3:15])[O:16][CH3:17])[C@H:10]([OH:19])[C@@H:9]([N:20]([C:28]3[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=3)[CH2:21][C:22]3[N:23]=[N:24][N:25]([CH3:27])[N:26]=3)[C:8]=2[CH:35]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 69218991HCID 69218991, compound

Product 1

HCID 69217216HCID 69217216, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 887MethanolSolvent

Procedure

(2R,3R,4S)-6-nitro-4-[N-(4-chlorophenyl)-N-(2-methyl-2H-tetrazol-5-ylmethyl)amino]-3-hydroxy-2-methyl-2-dimethoxymethyl-3,4-dihydro-2H-1-benzopyran (100 mg, 0.2 mmol) prepared in example 107 was dissolved in methanol (2 ml), thereto Cu(OAc)2 aqueous solution (0.38 ml, 0.4 M aqueous solution, 0.15 mmol) was added. Sodium borohydride (NaBH4, 113 mg, 3.0 mmol) was slowly added to the solution at the room temperature for 30 min. The reaction mixture was stirred for 1 hour, thereto ethyl acetate (5 ml) was added. The reaction mixture was filtered to remove the black precipitation. NaHCO3 aqueous solution (5 ml) was added to the resultant filtrate. The filtrate was extracted with ethyl acetate (30 ml). The organic layer was washed with saturated brine solution, dried over magnesium sulfate and concentrated. The crude product was purified by silica gel column chromatography (developing solvent-n-hexane:ethyl acetate=1:3), to give desired compound (60 mg, yield: 63%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove
  3. customthe black precipitation
  4. additionNaHCO3 aqueous solution (5 ml) was added to the resultant filtrate
  5. extractionThe filtrate was extracted with ethyl acetate (30 ml)
  6. washThe organic layer was washed with saturated brine solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel column chromatography (developing solvent-n-hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-20727b741434400abac2fe2fb6ac8c2f
Source dataset
uspto-grants-2008_08
Patent number
US07414068B2

Reaction notes

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