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

HRID 1860098Notes

Reaction equation

HRID 1860098 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[N+:22]([O-:24])=[O:23].O[CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].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>[C:31]([O:30][C:29]([NH:28][CH2:27][CH2:26][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[N+:22]([O-:24])=[O:23])=[O:35])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 5462977Diethyl azodicarboxylateHCID 18625703Ethyl 3-(4-hydroxy-3-nitrophenyl)-2-phenoxypropionate

Product 1

HCID 18625870Ethyl 3-[4-(2-t-butoxycarbonylaminoethoxy)-3-nitrophenyl]-2-phenoxypropionateYield 90.3%

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-(4-hydroxy-3-nitrophenyl)-2-phenoxypropionate (270 mg), which is the product of Reference example 53(a), t-butyl 2-hydroxyethylcarbamate (322 mg), triphenylphosphine (535 mg) and a solution of diethylazodicarboxylate in toluene (40%, 0.93 ml) and the reaction mixture was treated to afford the desired compound (349 mg) as a colorless oil.

Sources & evidence

ORD record
ord-3bca17a022f84026a4721f5bdbda2aef
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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