Triphenylphosphine → HCID 57595509, compound

HRID 1786064Notes

Reaction equation

HRID 1786064 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]([C@H:41]2[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[N:44]([C:51](=[O:59])[C:52]3[CH:57]=[CH:56][C:55](O)=[CH:54][CH:53]=3)[C@@H:43]([CH3:60])[CH2:42]2)[C:38](=[O:40])[CH3:39])=[CH:33][CH:32]=1.CCOC(/N=N/C(OCC)=O)=O>C1C=CC=CC=1>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([N:37]([C@H:41]2[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[N:44]([C:51](=[O:59])[C:52]3[CH:57]=[CH:56][C:55]([O:1][CH2:2][CH2:3][CH2:4][N:5]4[CH2:9][CH2:8][CH2:7][C:6]4=[O:10])=[CH:54][CH:53]=3)[C@@H:43]([CH3:60])[CH2:42]2)[C:38](=[O:40])[CH3:39])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5667441-(3-Hydroxypropyl)pyrrolidin-2-oneHCID 5462977Diethyl azodicarboxylateHCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

Product 1

HCID 57595509HCID 57595509, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(3-hydroxypropyl)-2-pyrrolidone was dissolved in benzene at room temperature with PPh3 (0.044 g, 0.16 mmol) added (2S,4R)-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.100 g, 0.22 mmol) and stirred for 5 min. DEAD (0.029 g, 0.16 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 45% 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 45% yield

Sources & evidence

ORD record
ord-929131b2e5ac4ecea524a088d0a2322f
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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