Ammonia → HCID 69063678, compound

HRID 2221357Notes

Reaction equation

HRID 2221357 reaction equation
[NH3:1].[CH2:2]([NH:9][C:10](=[O:25])[CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[O:18][C:17]([CH3:23])([CH3:22])[CH:16]3[O:24][CH:15]3[C:14]=2[CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O>C(O)C>[NH2:1][CH:15]1[C:14]2[C:19](=[CH:20][CH:21]=[C:12]([CH2:11][C:10]([NH:9][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[O:25])[CH:13]=2)[O:18][C:17]([CH3:23])([CH3:22])[CH:16]1[OH:24]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 86599516HCID 86599516, compound

Product 1

HCID 69063678HCID 69063678, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

250 ml of a 25%-strength aqueous ammonia solution was added to a solution of 35 g of the N-benzyl-2-(2,2-dimethyl-1a,7b-dihydro-2H-oxireno[c]chromen-6-yl)acetamide obtained above in 250 ml ethanol, and the mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into 500 ml water and extracted with 250 ml dichloromethane. The organic phase was separated, dried over sodium sulfate and largely evaporated under reduced pressure. 200 ml diethyl ether was added to the remaining residue. The crystals produced after a while were removed by suction and dried on a rotary evaporator at 60° C. and 20 bar. 11 g 2-(4-amino-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-N-benzylacetamide was obtained as grey solid, which was used without further purification or characterization for the subsequent reaction.

Workup

  1. extractionextracted with 250 ml dichloromethane
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. customlargely evaporated under reduced pressure
  5. addition200 ml diethyl ether was added to the remaining residue
  6. customThe crystals produced after a while
  7. customwere removed by suction
  8. customdried on a rotary evaporator at 60° C.

Sources & evidence

ORD record
ord-c0938f2939c04e1e8dd1fb7848b2f071
Source dataset
uspto-grants-2008_05
Patent number
US07368582B2

Reaction notes

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