Triphenylphosphine → Ethyl 3-[3-bromo-4-(2-t-butoxycarbonylaminoethoxy)phenyl]-2-phenoxypropionate

HRID 1860096Notes

Reaction equation

HRID 1860096 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].O[CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH2:24][CH2:25][NH:26][C:27]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:33]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 5462977Diethyl azodicarboxylateHCID 18625875Ethyl 3-(3-bromo4-hydroxyphenyl)-2-phenoxypropionate

Product 1

HCID 18626002Ethyl 3-[3-bromo-4-(2-t-butoxycarbonylaminoethoxy)phenyl]-2-phenoxypropionateYield 89.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a similar manner to that described in Example 122, a reaction was carried out using ethyl 3-(3-bromo-4-hydroxyphenyl)-2-phenoxypropionate (374 mg), which is the product of Reference example 52(a), t-butyl 2-hydroxyethylcarbamate (403 mg), triphenylphosphine (672 mg) and a solution of diethylazodicarboxylate in toluene (40%, 1.16 ml) and the reaction mixture was treated to afford the desired compound (466 mg) as a colorless oil.

Sources & evidence

ORD record
ord-15be501d351b498db78689d6f6c77635
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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