Triphenylphosphine → [Rac]-2-methoxy-3-(4-{2-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-naphthalen-1-yl)-propionic acid methyl ester

HRID 479172Notes

Reaction equation

HRID 479172 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:17][CH3:18])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[CH:8][CH:7]=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[O:29][C:30]([CH3:36])=[C:31]([CH2:33][CH2:34]O)[N:32]=2)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:17][CH3:18])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([O:16][CH2:34][CH2:33][C:31]2[N:32]=[C:28]([C:25]3[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=3)[O:29][C:30]=2[CH3:36])=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 107520982-[2-(4-Methoxyphenyl)-5-methyloxazol-4-yl]ethanolHCID 69557756[Rac]-3-(4-hydroxy-naphthalen-1-yl)-2-methoxy-propionic acid methyl ester

Product 1

HCID 69557970[Rac]-2-methoxy-3-(4-{2-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-naphthalen-1-yl)-propionic acid methyl ester

Procedure

In analogy to the procedure described in example 17 a], [rac]-3-(4-hydroxy-naphthalen-1-yl)-2-methoxy-propionic acid methyl ester was reacted with 2-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-ethanol [J. Med. Chem. (1998), 41(25), 5037-5054] in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-2-methoxy-3-(4-{2-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-naphthalen-1-yl)-propionic acid methyl ester, which was further saponified in analogy to the procedure described in example 91 e] to yield [rac]-2-methoxy-3-(4-{2-[2-(4-methoxy-phenyl-5-methyl-oxazol-4-yl]-ethoxy}-naphthalen-1-yl)-propionic acid as colorless solid.

Sources & evidence

ORD record
ord-04bf7888433345cab204c1964f87fa35
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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