25279-63-4 → HCID 68817098, compound

HRID 511733Notes

Reaction equation

HRID 511733 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:37]=[C:38]([N+:40]([O-])=O)[CH:39]=1)[C:7]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)=[O:8])([O-])=O>CN(C)C=O.O.[Zn]>[NH2:40][C:38]1[CH:37]=[C:6]([CH:5]=[C:4]([NH2:1])[CH:39]=1)[C:7]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)=[O:8]

Participants

5

Reactant 1

HCID 2111671025279-63-4

Product 1

HCID 68817098HCID 68817098, compoundYield 80.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

11.42 g (19.66 mmol) of (3-β)-cholest-5-en-3-yl 3,5-dinitrobenzoate are dissolved in a mixture of 54 mL of N,N-dimethylformamide and 6 mL water. 32.6 g (120 mmol) ferric chloride hexahydrate are added. 13.1 g (201 mmol) zinc powder is added portion wise within 60 minutes. The mixture is allowed to react for 2 hours. The reaction mixture is partitioned between ethyl acetate and water and filtrated. The organic phase is washed repeatedly with water, dried over sodium sulfate, filtrated and concentrated under reduced pressure. Filtration of the residue on 400 g silica gel using toluene:ethyl acetate 1:3 as eluent and crystallization from ethyl acetate:hexane mixture yielded 8.20 g of (3-β)-cholest-5-en-3-yl 3,5-diaminobenzoate as yellowish crystals.

Workup

  1. customto react for 2 hours
  2. customThe reaction mixture is partitioned between ethyl acetate and water
  3. filtrationfiltrated
  4. washThe organic phase is washed repeatedly with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure
  8. filtrationFiltration of the residue on 400 g silica gel
  9. customcrystallization from ethyl acetate

Sources & evidence

ORD record
ord-9d49784146534a8ca019414a4dd69713
Source dataset
uspto-grants-2015_08
Patent number
US09097938B2

Reaction notes

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