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

HRID 987148Notes

Reaction equation

HRID 987148 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][CH:21]([CH2:27][C:28]1[CH:33]=[CH:32][C:31](O)=[CH:30][CH:29]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:19].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:1]([O:5][C:6]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][O:16][C:31]2[CH:30]=[CH:29][C:28]([CH2:27][CH:21]([O:20][CH2:18][CH3:19])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:33][CH:32]=2)=[CH:12][CH:13]=1)=[O:17])([CH3:4])([CH3:2])[CH3:3]

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

Compound (c) (1.03 g; 4.34 mmole) and (b) (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 the desired product

Workup

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

Sources & evidence

ORD record
ord-ec61ce6bcf5f40698eb53e7815ac06ad
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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