Triphenylphosphine → HCID 68616678, compound

HRID 394285Notes

Reaction equation

HRID 394285 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])=[C:9]([F:14])[CH:8]=1)[CH3:2].[C:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[S:30][C:31]([CH2:35]O)=[C:32]([CH3:34])[N:33]=2)=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[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][CH2:35][C:31]2[S:30][C:29]([C:26]3[CH:27]=[CH:28][C:23]([C:19]([CH3:21])([CH3:20])[CH3:22])=[CH:24][CH:25]=3)=[N:33][C:32]=2[CH3:34])=[C:9]([F:14])[CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22647417HCID 22647417, compoundHCID 68618019[Rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester

Product 1

HCID 68616678HCID 68616678, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to the procedure described in example 1 d], [rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (example 7 a]) was reacted with [2-(4-tert-butyl-phenyl)-4-methyl-thiazol-5-yl]-methanol in tetrahydrofuran in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-3-{4-[2-(4-tert-butyl-phenyl)-4-methyl-thiazol-5-ylmethoxy]-3-fluoro-phenyl}-2-ethoxy-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 4 e], to yield [rac]-3-{4-[2-(4-tert-butyl-phenyl)-4-methyl-thiazol-5-ylmethoxy]-3-fluoro-phenyl}-2-ethoxy-propionic acid as a light yellow solid.

Workup

  1. customdescribed in example 1 d

Sources & evidence

ORD record
ord-65e17138ca604c43b4880511c34426c2
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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