Triphenylphosphine → HCID 22988457, compound

HRID 987133Notes

Reaction equation

HRID 987133 reaction equation
[C:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].O[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])=[CH:22][CH:21]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:1]([CH:3]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])=[CH:22][CH:21]=2)=[CH:14][CH:15]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 15317953HCID 15317953, compoundHCID 22988433HCID 22988433, compound

Product 1

HCID 22988457HCID 22988457, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-cyano-3-(4-hydroxyphenyl)propanoate (1 g, 4.56 mmol) and N-[4-(2-hydroxyethyl)phenyl]-2-methylpropanamide (1.42 g, 6.85 mmol) were mixed in dichloromethane (40 ml). 1,1′-(Azodicarbonyl)dipiperidine (2.3 g, 9.12 mmol) and triphenylphosphine (2.4 g, 9.15 mmol) were then added respectively. The mixture was stirred overnight and filtered. The filtrate was evaporated to dry in vacuum. Column chromatography of the residue on silica gel using ethyl acetate/heptane as eluant gave 0.5 g desired product, yield 27%.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customto dry in vacuum

Sources & evidence

ORD record
ord-14481541886147bd82a30d632f3bbac9
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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