Triphenylphosphine → HCID 53920635, compound

HRID 987305Notes

Reaction equation

HRID 987305 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14](=[O:27])[CH:15]([O:24][CH2:25][CH3:26])[CH2:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=1)[CH3:12].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:11]([O:13][C:14](=[O:27])[CH:15]([O:24][CH2:25][CH3:26])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][C:2]([NH2:1])=[CH:3][CH:4]=2)=[CH:19][CH:18]=1)[CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 669044-Aminophenethyl alcoholHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 53920635HCID 53920635, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Aminophenethyl alcohol (1.39 g; 10.2 mmole) and 2-ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester (described in Example 20b) (2.42 g; 10.2 mmole) were dissolved in dichloromethane (35 ml) under argon at room temperature. Azodicarbonyl dipiperidine (3.85 g; 15.2 mmole) and thereafter triphenylphosphine (3.20 g; 12.2 mmole) were added. After stirring at room temperature for 1 minute dichloromethane (30 ml) was added and after 21 hours the solvent was evaporated in vacuo. Purification by chromatography on silica gel using heptane:ethyl acetate (3:2) as eluant gave 3.12 g (yield 86%) of 3-{4-[2-(4-aminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester.

Workup

  1. additionwas added and after 21 hours the solvent
  2. customwas evaporated in vacuo
  3. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-b1ad970d3be949aebbe7a119c432a12d
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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