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

HRID 479171Notes

Reaction equation

HRID 479171 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.C(OC(CC1C2SC=CC=2C(O[CH2:38][CH2:39][C:40]2[N:41]=[C:42]([C:46]3[CH:51]=[CH:50][C:49]([F:52])=[CH:48][C:47]=3[O:53][CH2:54][CH3:55])[O:43][C:44]=2[CH3:45])=CC=1)C(O)=O)C.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][CH2:38][CH2:39][C:40]2[N:41]=[C:42]([C:46]3[CH:51]=[CH:50][C:49]([F:52])=[CH:48][C:47]=3[O:53][CH2:54][CH3:55])[O:43][C:44]=2[CH3:45])=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18003586[Rac]-2-ethoxy-3-(4-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy-}-benzo[b]thiophen-7-yl)-propionic acidHCID 69557756[Rac]-3-(4-hydroxy-naphthalen-1-yl)-2-methoxy-propionic acid methyl ester

Product 1

HCID 69555691[Rac]-3-(4-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-naphthalen-1-yl)-2-methoxy-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-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethanol (example 95) in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-3-(4-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-naphthalen-1-yl)-2-methoxy-propionic acid methyl ester, which was further saponified in analogy to the procedure described in example 91 e] to yield [rac]-3-(4-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-naphthalen-1-yl)-2-methoxy-propionic acid as colorless solid.

Sources & evidence

ORD record
ord-f22a93e11c71484a83efa3346ba3d8b0
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

Loading…