Triphenylphosphine → [Rac]-3-{4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid ethyl ester

HRID 2215220Notes

Reaction equation

HRID 2215220 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:14])[CH3:2].[C:19]([C:23]1[O:24][C:25]([CH3:31])=[C:26]([CH2:28][CH2:29]O)[N:27]=1)([CH3:22])([CH3:21])[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:29][CH2:28][C:26]2[N:27]=[C:23]([C:19]([CH3:20])([CH3:22])[CH3:21])[O:24][C:25]=2[CH3:31])=[CH:9][C:8]=1[CH3:14])[CH3:2]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 115792322-(2-Tert-butyl-5-methyl-oxazol-4-yl)-ethanolHCID 57792490[Rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester

Product 1

HCID 69486911[Rac]-3-{4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid ethyl ester

Procedure

In analogy to the Mitsunobu-procedure described in example 1, step f, [rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester (example 46 b]) was reacted with 2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethanol (example 1, step e]) in the presence of triphenylphosphine and di-tert-butyl azodicarboxylate to yield [rac]-3-{4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid ethyl ester as colorless oil.

Sources & evidence

ORD record
ord-2adf1e31e64a4aa282676a546d787523
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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