Sodium Chloride → HCID 10387945, compound

HRID 2260585Notes

Reaction equation

HRID 2260585 reaction equation
[C:1]([C:4]1[CH:33]=[CH:32][C:7]2[O:8][CH2:9][C:10]3[CH:31]=[CH:30][CH:29]=[CH:28][C:11]=3[CH:12]([C:13]([NH:15][C:16]3[C:21]([CH:22]([CH3:24])[CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=3[CH:25]([CH3:27])[CH3:26])=[O:14])[C:6]=2[CH:5]=1)(O)=[O:2].ClC(OCC)=O.[BH4-].[Na+].[Cl-].[Na+]>O1CCCC1.C(N(CC)CC)C>[OH:2][CH2:1][C:4]1[CH:33]=[CH:32][C:7]2[O:8][CH2:9][C:10]3[CH:31]=[CH:30][CH:29]=[CH:28][C:11]=3[CH:12]([C:13]([NH:15][C:16]3[C:17]([CH:25]([CH3:26])[CH3:27])=[CH:18][CH:19]=[CH:20][C:21]=3[CH:22]([CH3:24])[CH3:23])=[O:14])[C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 10388689HCID 10388689, compound

Product 1

HCID 10387945HCID 10387945, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

After 1.33 g of 2-ocarboxy-6,11-dihydro-N-(2,6-diisopropylphenyl)dibenz[b,e]oxepin-11-carboxamide (Compound 25) obtained in Example 25 was dissolved in 10 ml of tetrahydrofuran, 1.0 ml of triethylamine and 0.39 g of ethyl chloroformate were added to the solution under ice cooling. The mixture was stirred at room temperature for 12 hours. Then 0.57 g of sodium borohydride was slowly added to the reaction mixture under ice cooling. After stirring at room temperature for 6 hours, saturated aqueous sodium chloride solution was added and the mixture was extracted with ethyl acetate. After drying over anhydrous magnesium sulfate, the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (2:1)]. The crude crystal was recrystallized from ethyl acetate-hexane to obtain 1.08 g of Compound 26 as white needles.

Workup

  1. stirringAfter stirring at room temperature for 6 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (2:1)]
  6. customThe crude crystal was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-cae6ac6c02ec4b108b5bcfe11aad221f
Source dataset
uspto-grants-1995_12
Patent number
US05478835

Reaction notes

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