Triphenylphosphine → (2S,4R)-N-(4-Chloro-phenyl)-N-{1-[4-(3-imidazol-1-yl-3-methyl-butoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide

HRID 1786012Notes

Reaction equation

HRID 1786012 reaction equation
[N:1]1([C:6]([CH3:11])([CH3:10])[CH2:7][CH2:8][OH:9])[CH:5]=[CH:4][N:3]=[CH:2]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]([C@H:42]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]([C:52](=[O:60])[C:53]3[CH:58]=[CH:57][C:56](O)=[CH:55][CH:54]=3)[C@@H:44]([CH3:61])[CH2:43]2)[C:39](=[O:41])[CH3:40])=[CH:34][CH:33]=1.CCOC(/N=N/C(OCC)=O)=O>C1C=CC=CC=1>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([N:38]([C@H:42]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]([C:52](=[O:60])[C:53]3[CH:58]=[CH:57][C:56]([O:9][CH2:8][CH2:7][C:6]([N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)([CH3:11])[CH3:10])=[CH:55][CH:54]=3)[C@@H:44]([CH3:61])[CH2:43]2)[C:39](=[O:41])[CH3:40])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 187223133-Imidazol-1-yl-3-methyl-butan-1-olHCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

Product 1

HCID 57595483(2S,4R)-N-(4-Chloro-phenyl)-N-{1-[4-(3-imidazol-1-yl-3-methyl-butoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamideYield 46%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Imidazol-1-yl-3-methyl-butan-1-ol was dissolved in benzene at room temperature with PPh3 (0.088 g, 0.33 mmol) added (2S,4R)-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.133 g, 0.30 mmol) and stirred for 5 min. DEAD (0.058 g, 0.33 mmol) was added and the reaction was stirred for 18 h at room temperature. The reaction was concentrated and purified by silica gel chromatography (4% MeOH/96% CH2Cl2 to 5% MeOH/95% CH2Cl2 to 6% MeOH/94% CH2Cl2) to afford the product in 46% yield

Workup

  1. stirringthe reaction was stirred for 18 h at room temperature
  2. concentrationThe reaction was concentrated
  3. custompurified by silica gel chromatography (4% MeOH/96% CH2Cl2 to 5% MeOH/95% CH2Cl2 to 6% MeOH/94% CH2Cl2)
  4. customto afford the product in 46% yield

Sources & evidence

ORD record
ord-53b6a1d374464c7dadaa4a3f7b6367b9
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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