Triphenylphosphine → Ethyl 3-[4-(2-t-butoxycarbonylaminoethoxy)phenyl]-2-(4-chlorophenoxy)propionate

HRID 1860074Notes

Reaction equation

HRID 1860074 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.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>>[C:29]([O:28][C:27]([NH:26][CH2:25][CH2:24][O:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH:7]([O:6][C:5]2[CH:21]=[CH:22][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:19][CH:18]=1)=[O:33])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 5462977Diethyl azodicarboxylateHCID 18625838Ethyl 2-(4-chlorophenoxy)-3-(4-hydroxyphenyl)propionate

Product 1

HCID 18625883Ethyl 3-[4-(2-t-butoxycarbonylaminoethoxy)phenyl]-2-(4-chlorophenoxy)propionateYield 78%

Procedure

In a similar manner to that described in Example 122, a reaction was carried out using ethyl 2-(4-chlorophenoxy)-3-(4-hydroxyphenyl)propionate (1.01 g), which is the product of Reference example 38(b), t-butyl 2-hydroxyethylcarbamate (1.27 g), triphenylphosphine (2.06 g) and diethylazodicarboxylate (1.37 g) and the reaction mixture was treated to afford the title compound (1.14 g) as a colorless oil.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-b3f1a6cd53d8446f9aef78b8c2d0f225
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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