Triphenylphosphine → HCID 54139684, compound

HRID 987313Notes

Reaction equation

HRID 987313 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].O[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])=[CH:23][CH:22]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])=[CH:23][CH:22]=2)=[CH:11][CH:12]=1)[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 22988433HCID 22988433, compound

Product 1

HCID 54139684HCID 54139684, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester (described in Example 20b) (0.71 g; 2.97 mmole) dissolved in dichloromethane (5 ml) was added to a mixture of N-[4-(2-hydroxyethyl)phenyl]isobutyramide (0.5 g; 2.47 mmole), azodicarbonyl dipiperidine (0.75 g; 2.97 mmole) and triphenylphosphine (0.78 g; 2.97 mmole) in dichloromethane (15 ml). After stirring at room temperature over night the reaction mixture was filtered and the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel using heptane:ethyl acetate (gradient 3:1 to 1:1) as eluant to give 0.69 g (yield 65%) of 2-ethoxy-3-{4-[2-(4-isobutyrylaminophenyl)ethoxy]phenyl}propanoic acid ethyl ester.

Workup

  1. filtrationwas filtered
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-01629895e45246d7b280ffcaad158450
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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