Ammonia → HCID 69061410, compound

HRID 2221353Notes

Reaction equation

HRID 2221353 reaction equation
[NH3:1].[CH3:2][C:3]1([CH3:28])[CH:12]2[O:13][CH:11]2[C:10]2[CH:9]=[C:8]([CH2:14][C:15]([NH:17][CH:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[O:16])[CH:7]=[CH:6][C:5]=2[O:4]1.ClCCl.CO>C(O)C.O>[NH2:1][CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:14][C:15]([NH:17][CH:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[O:16])[CH:9]=2)[O:4][C:3]([CH3:28])([CH3:2])[CH:12]1[OH:13]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 6344DichloromethaneHCID 86599514HCID 86599514, compound

Product 1

HCID 69061410HCID 69061410, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

88 ml of a 25%-strength aqueous ammonia solution was added to a solution of 16 g of the 2-(2,2-dimethyl-1a,7b-dihydro-2H-oxireno[c]chromen-6-yl)-N-1,2,3,4-tetrahydronaphth-1-yl acetamide obtained above in 88 ml ethanol, and the mixture was stirred for 18 hours at room temperature. Then 200 ml dichloromethane and 50 ml methanol were added thereto, and the mixture was stirred for a further 15 minutes. Then 200 ml water was added and the mixture was again stirred for 15 minutes. The organic phase was separated and largely evaporated at reduced pressure. The remaining residue was stirred with 30 ml of ethyl acetate, filtered and dried on a rotary evaporator at 70° C. and 20 bar. 3.1 g 2-(4-amino-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-N-1,2,3,4-tetrahydronaphth-1-yl acetamide was obtained as grey solid, which was used without further purification for the subsequent reaction.

Workup

  1. stirringthe mixture was stirred for a further 15 minutes
  2. stirringthe mixture was again stirred for 15 minutes
  3. customThe organic phase was separated
  4. customlargely evaporated at reduced pressure
  5. stirringThe remaining residue was stirred with 30 ml of ethyl acetate
  6. filtrationfiltered
  7. customdried on a rotary evaporator at 70° C.

Sources & evidence

ORD record
ord-40bc589167b24aa790226d120943aa05
Source dataset
uspto-grants-2008_05
Patent number
US07368582B2

Reaction notes

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