Ammonia → HCID 67916906, compound

HRID 1196519Notes

Reaction equation

HRID 1196519 reaction equation
C(O)(=O)/C=C\C(O)=O.[Cl:9][C:10]1[CH:11]=[C:12]([CH2:17][C:18]([N:20]2[CH2:25][CH2:24][C@H:23]([C:26]([O:28]C)=O)[CH2:22][C@@H:21]2[CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:19])[CH:13]=[CH:14][C:15]=1[Cl:16].[NH3:36]>C(O)C>[ClH:9].[Cl:9][C:10]1[CH:11]=[C:12]([CH2:17][C:18]([N:20]2[CH2:25][CH2:24][C@H:23]([C:26]([NH2:36])=[O:28])[CH2:22][C@@H:21]2[CH2:30][N:31]2[CH2:32][CH2:33][CH2:34][CH2:35]2)=[O:19])[CH:13]=[CH:14][C:15]=1[Cl:16]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 131717373HCID 131717373, compound

Product 1

HCID 67916906HCID 67916906, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Example 3 as the free base (0.25 g) in a mixture of ethanol (5 ml) and liquid ammonia (50 ml) was heated at 100° for 3 days in an autoclave. The solvent was evaporated and the residue was purified by flash chromatography eluting with dichloromethane/methanol/ammonia 100:10:2 as eluent to give the free base of the title compound as an oil (0.14 g). A solution of the oil in a mixture of diethyl ether and methyl acetate was treated with ethereal hydrogen chloride. The resulting solid was washed with diethyl ether and dried to give the title compound as a solid (0.065 g) T.l.c. Silica, Dichloromethane/ethanol/ammonia (75:10:2) Rf 0.45.

Workup

  1. temperaturewas heated at 100° for 3 days in an autoclave
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography
  4. washeluting with dichloromethane/methanol/ammonia 100:10:2 as eluent

Sources & evidence

ORD record
ord-fd9c79fd43ef4a579f55f20487361af9
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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