Triphenylphosphine → (-)-4'-{2-[4-(4-Nitrobenzyl)-2,5-dioxoimidazolidinyl]ethyl}acetanilide

HRID 483372Notes

Reaction equation

HRID 483372 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[N+:13]([C:16]1[CH:29]=[CH:28][C:19]([CH2:20][CH:21]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[NH:22]2)=[CH:18][CH:17]=1)([O-:15])=[O:14].O[CH2:31][CH2:32][C:33]1[CH:42]=[CH:41][C:36]([NH:37][C:38](=[O:40])[CH3:39])=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC>[N+:13]([C:16]1[CH:29]=[CH:28][C:19]([CH2:20][CH:21]2[C:25](=[O:26])[N:24]([CH2:31][CH2:32][C:33]3[CH:42]=[CH:41][C:36]([NH:37][C:38](=[O:40])[CH3:39])=[CH:35][CH:34]=3)[C:23](=[O:27])[NH:22]2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3295905N-[4-(2-hydroxyethyl)phenyl]acetamideHCID 5462977Diethyl azodicarboxylateHCID 104665795-[(4-Nitrophenyl)methyl]imidazolidine-2,4-dione

Product 1

HCID 19752550(-)-4'-{2-[4-(4-Nitrobenzyl)-2,5-dioxoimidazolidinyl]ethyl}acetanilideYield 71.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of diethylazodicarboxylate (7.8 g) in DME (40 ml) was added dropwise under N2 to a stirred mixture of the product from step (a) (10.5 g), the product from step (c) (8.0 g) and triphenylphosphine (11.7 g) in DME (400 ml). When addition was complete, the mixture was stirred at room temperature for 17 hours, then evaporated in vacuo and the residue crystallised from ethanol/ether (1:4 v/v) to give the desired product as a pale yellow solid (12.7 g), [α]D25 -97.8° (c=0.50, MeOH).

Workup

  1. additionWhen addition
  2. customevaporated in vacuo
  3. customthe residue crystallised from ethanol/ether (1:4 v/v)

Sources & evidence

ORD record
ord-7b7f32cdc2c7499fab5cf10b83476cad
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

Loading…