Ammonium Chloride → Cholest-5-en-3-yl 2-(4-aminobenzyl)-3-(4-aminophenyl)propanoate

HRID 2090150Notes

Reaction equation

HRID 2090150 reaction equation
[N+:1]([C:4]1[CH:51]=[CH:50][C:7]([CH2:8][CH:9]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([N+:47]([O-])=O)=[CH:43][CH:42]=2)[C:10]([O:12][CH:13]2[CH2:37][CH2:36][C@@:35]3([CH3:38])[C:15](=[CH:16][CH2:17][C@@H:18]4[C@@H:34]3[CH2:33][CH2:32][C@@:31]3([CH3:39])[C@H:19]4[CH2:20][CH2:21][C@@H:22]3[C@H:23]([CH3:30])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:14]2)=[O:11])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>[Zn].CO.O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=2)[C:10]([O:12][CH:13]2[CH2:37][CH2:36][C@@:35]3([CH3:38])[C:15](=[CH:16][CH2:17][C@@H:18]4[C@@H:34]3[CH2:33][CH2:32][C@@:31]3([CH3:39])[C@H:19]4[CH2:20][CH2:21][C@@H:22]3[C@H:23]([CH3:30])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:14]2)=[O:11])=[CH:50][CH:51]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86602370Cholest-5-en-3-yl 2-(4-nitrobenzyl)-3-(4-nitrophenyl)propanoate

Product 1

HCID 67348705Cholest-5-en-3-yl 2-(4-aminobenzyl)-3-(4-aminophenyl)propanoateYield 69.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

2.62 g (3.75 mmol) Cholest-5-en-3-yl 2-(4-nitrobenzyl)-3-(4-nitrophenyl)-propanoate and 0.79 g (14.77 mmol) ammonium chloride were suspended in 90 ml of a mixture consisting of methanol:water 9:1. 4.90 g (74.96 mmol) zinc powder was then added in 10 minutes. The reaction mixture was then allowed to react at 45° C. for 6 hours and partitioned between dichloromethane and water; the organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. First chromatography of the residue on 50 g silica gel using toluene:ethyl acetate 1:1 as eluant and second chromatography on 50 g silica gel using tert.butyl methylether as eluant yielded 1.66 g Cholest-5-en-3-yl 2-(4-aminobenzyl)-3-(4-aminophenyl)-propanoate as white powder.

Workup

  1. customto react at 45° C. for 6 hours
  2. custompartitioned between dichloromethane and water
  3. washthe organic phase was washed repeatedly with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-95ab636b149d4a84b6ae8b73526f61ab
Source dataset
uspto-grants-2013_05
Patent number
US08436132B2

Reaction notes

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