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

HRID 1860094Notes

Reaction equation

HRID 1860094 reaction equation
[Cl: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>[C:29]([O:28][C:27]([NH:26][CH2:25][CH2:24][O:8][C:7]1[CH:6]=[CH:5][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:3][C:2]=1[Cl:1])=[O:33])([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 5462977Diethyl azodicarboxylateHCID 18625720Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-phenoxypropionate

Product 1

HCID 18625902Ethyl 3-[4-(2-t-butoxycarbonylaminoethoxy)-3-chlorophenyl]-2-phenoxypropionateYield 93.6%

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-chloro-4-hydroxyphenyl)-2-phenoxypropionate (761 mg), which is the product of Reference example 51(a), t-butyl 2-hydroxyethylcarbamate (0.96 g), triphenylphosphine (1.55 g) and solution of diethylazodicarboxylate in toluene (40%, 2.69 ml) and the reaction mixture was treated to afford the desired compound (1.03 g) as a colorless oil.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-65f605a237f348d6b5421842762bf5da
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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