Water → HCID 68517535, compound

HRID 1717267Notes

Reaction equation

HRID 1717267 reaction equation
[N:1]([C:4]1[CH:21]=[CH:20][C:7]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].O=[C:23]([CH2:30][CH2:31][CH3:32])[CH2:24][C:25]([O:27]CC)=[O:26].[O-]CC.[Na+].O>C(O)C>[C:14]1([CH2:13][CH2:12][CH2:11][NH:10][C:8]([C:7]2[CH:20]=[CH:21][C:4]([N:1]3[C:23]([CH2:30][CH2:31][CH3:32])=[C:24]([C:25]([OH:27])=[O:26])[N:3]=[N:2]3)=[CH:5][CH:6]=2)=[O:9])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 238498Ethyl 3-oxohexanoateHCID 2723922Sodium ethoxideHCID 86629798HCID 86629798, compound

Product 1

HCID 68517535HCID 68517535, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The pale-yellow solid of 4-azido-N-(3-phenylpropyl)benzamide obtained in Example 60a) and ethyl 3-oxohexanoate (1.08 ml, 6.43 mmol, 1.25 eq.) were dissolved in ethanol (20 ml), sodium ethoxide (486 mg, 6.43 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 10 min, and then at 60° C. for 13 hr. Water (20 ml) was added to the reaction mixture, ethanol was evaporated, and the residue was diluted with 2% aqueous sodium carbonate solution (20 ml) and washed with ethyl acetate-hexane (2:1, 50 ml). The organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml). The aqueous layers were combined, washed with ethyl acetate-hexane (1:1, 30 ml), acidified with 6N hydrochloric acid and stood still at 0° C. The precipitate was collected by filtration, washed with ice-cold water and dried to give the title compound as a grayish white powder (1.99 g, 5.07 mmol, 98.7%)

Workup

  1. waitat 60° C. for 13 hr
  2. customwas evaporated
  3. additionthe residue was diluted with 2% aqueous sodium carbonate solution (20 ml)
  4. washwashed with ethyl acetate-hexane (2:1, 50 ml)
  5. extractionThe organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml)
  6. washwashed with ethyl acetate-hexane (1:1, 30 ml)
  7. customstood still at 0° C
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with ice-cold water
  10. customdried

Sources & evidence

ORD record
ord-cd80b1cf0aae44e3a171a662af21355d
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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