Cholesterol → Cholest-5-en-3-yl 2-(4-nitrobenzyl)-3-(4-nitrophenyl)propanoate

HRID 2090149Notes

Reaction equation

HRID 2090149 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][C:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)(C(O)=O)[C:10](O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:28][CH:29]([CH2:31][CH2:32][CH2:33][C@H:34]([C@@H:36]1[C@:53]2([CH3:54])[C@H:39]([C@H:40]3[C@H:50]([CH2:51][CH2:52]2)[C@:48]2([CH3:49])[C:43]([CH2:44][C@@H:45]([OH:55])[CH2:46][CH2:47]2)=[CH:42][CH2:41]3)[CH2:38][CH2:37]1)[CH3:35])[CH3:30]>CN(C)C1C=CN=CC=1.ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:10]([O:55][CH:45]2[CH2:46][CH2:47][C@@:48]3([CH3:49])[C:43](=[CH:42][CH2:41][C@@H:40]4[C@@H:50]3[CH2:51][CH2:52][C@@:53]3([CH3:54])[C@H:39]4[CH2:38][CH2:37][C@@H:36]3[C@H:34]([CH3:35])[CH2:33][CH2:32][CH2:31][CH:29]([CH3:28])[CH3:30])[CH2:44]2)=[O:11])=[CH:26][CH:27]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 5997CholesterolHCID 229285922,2-Bis(4-nitrobenzyl)malonic acid

Product 1

HCID 86602370Cholest-5-en-3-yl 2-(4-nitrobenzyl)-3-(4-nitrophenyl)propanoateYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.00 g (5.34 mmol) of 2,2-bis(4-nitrobenzyl)malonic acid and 2.07 g (5.35 mmol) 5-cholesten-3β-ol and 65 mg (0.53 mmol) 4-dimethylaminopyridine in 40 ml of dichloromethane were cooled to 0° C. and 1.16 g (5.62 mmol) N,N′-dicyclohexylcarbodiimde were added. The mixture was subsequently allowed to react for 2 hours at 0° C. and 19 hours at 25° C., filtered and concentrated by rotary evaporation. Chromatography of the residue on 50 g silica gel using toluene as eluant and recrystallisation form ethyl acetate yielded 3.09 g (83%) Cholest-5-en-3-yl 2-(4-nitrobenzyl)-3-(4-nitrophenyl)propanoate as a white powder.

Workup

  1. addition1.16 g (5.62 mmol) N,N′-dicyclohexylcarbodiimde were added
  2. customto react for 2 hours at 0° C. and 19 hours at 25° C.
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customrecrystallisation form ethyl acetate

Sources & evidence

ORD record
ord-6f5e771717514f25a9e82d788d6fe0cf
Source dataset
uspto-grants-2013_05
Patent number
US08436132B2

Reaction notes

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