Triphenylphosphine → Ethyl 3-(4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoate

HRID 279680Notes

Reaction equation

HRID 279680 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([O:20][C:21](=[O:34])[CH:22]([O:31][CH2:32][CH3:33])[CH2:23][C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1)[CH3:19].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:18]([O:20][C:21](=[O:34])[CH:22]([O:31][CH2:32][CH3:33])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:16][CH2:15][CH2:14][C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:17])=[CH:13][CH:12]=2)=[CH:26][CH:25]=1)[CH3:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 11413715N-Boc-2-(4-aminophenyl)ethanolHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 22988408Ethyl 3-(4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoateYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-Hydroxyethyl)phenylcarbamic acid tert-butyl ester (1.03 g; 4.34 mmole) and 2-ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester (1.03 g; 4.34 mmole) were dissolved in dichloromethane under argon at room temperature. Azodicarbonyl dipiperidine (1.65 g, 6.5 mmole) and thereafter triphenylphosphine (1.37 g; 5.2 mmole) were added. After stirring at room temperature for 6 hours the solvent was evaporated in vacuo. Purification by chromatography on silica gel using heptane ethyl acetate (2:1) as eluant gave 1.78 g (yield 89%) of 3-{4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]-phenyl}-2-ethoxypropanoic acid ethyl ester.

Workup

  1. customwas evaporated in vacuo
  2. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-6f03c20a2eef4c928db9d909e658d2db
Source dataset
uspto-grants-2002_03
Patent number
US06362360B1

Reaction notes

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