HCID 19972553, compound → HCID 19972455, compound

HRID 1452340Notes

Reaction equation

HRID 1452340 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]([C:21]2[C:30]3[O:29][C:28]([C:31]4[CH:36]=[CH:35][C:34]([N+:37]([O-])=O)=[CH:33][CH:32]=4)=[C:27]([CH3:40])[C:26](=[O:41])[C:25]=3[CH:24]=[CH:23][CH:22]=2)=[O:20])[CH2:11][CH2:10]1>C(O)C.C(O)(=O)C.[Ni]>[NH2:37][C:34]1[CH:33]=[CH:32][C:31]([C:28]2[O:29][C:30]3[C:21]([C:19](=[O:20])[NH:18][CH2:17][CH2:16][CH2:15][N:12]4[CH2:13][CH2:14][N:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[O:2][CH3:1])[CH2:10][CH2:11]4)=[CH:22][CH:23]=[CH:24][C:25]=3[C:26](=[O:41])[C:27]=2[CH3:40])=[CH:36][CH:35]=1

Participants

5

Reactant 1

HCID 19972553HCID 19972553, compound

Product 1

HCID 19972455HCID 19972455, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

2.22 g of compound of Example 113 and 0.56 g of Raney-Nickel in 96 ml of ethanol and 4.8 ml of acetic acid was hydrogenated in a Parr apparatus (pH2 =1 atm) at room temperature. After 6 hours shaking, the catalyst was filtered off and the filtrate was alkalinized with 3N aqueous sodium hydroxide solution and diluted with water. After standing for 2 days at 0° C., the precipitated title compound was collected by suction, washed with water, desiccated and recrystallized firstly from ethyl acetate then from ethanol yielding 1.5 g of the title compound (m.p. 192°-194° C.).

Workup

  1. customwas hydrogenated in a Parr apparatus (pH2 =1 atm) at room temperature
  2. filtrationthe catalyst was filtered off
  3. additiondiluted with water
  4. waitAfter standing for 2 days at 0° C.
  5. customthe precipitated title compound
  6. customwas collected by suction
  7. washwashed with water
  8. customrecrystallized firstly from ethyl acetate

Sources & evidence

ORD record
ord-859312c39b764ca28124e15d97252b9b
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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