Triphenylphosphine → HCID 68616363, compound

HRID 394323Notes

Reaction equation

HRID 394323 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([O:16][CH2:17][CH3:18])[CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([OH:14])=[C:9]([F:15])[CH:8]=1)[CH3:2].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[S:28][C:29]([CH3:35])=[C:30]([CH2:32][CH2:33]O)[N:31]=2)=[CH:23][CH:22]=1.COC(=O)CC(=O)C(Br)C.ClC1C=CC(C(N)=S)=CC=1.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:19])[CH:5]([O:16][CH2:17][CH3:18])[CH2:6][C:7]1[CH:8]=[C:9]([F:15])[C:10]([O:14][CH2:33][CH2:32][C:30]2[N:31]=[C:27]([C:24]3[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=3)[S:28][C:29]=2[CH3:35])=[C:11]([F:13])[CH:12]=1)[CH3:2]

Participants

8

Reactant 6

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27348264-ChlorothiobenzamideHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 226476242-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-ethanolHCID 59419836Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)-2-ethoxypropanoate

Product 1

HCID 68616363HCID 68616363, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to the procedure described in example 4 d], [rac]-3-(3,5-difluoro-4-hydroxy-phenyl)-2-ethoxy-propionic acid ethyl ester [example 70 a]] was reacted with 2-[2-(4-chloro-phenyl)-5-methyl-thiazol-4-yl]-ethanol (prepared from [rac]-4-bromo-3-oxo-pentanoic acid methyl ester [PCT Int. Appl. (2001), WO 01/79202] and 4-chloro-thiobenzamide in analogy to the procedures described in examples 12 a] and 12 b]) in tetrahydrofuran in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-3-(4-{2-[2-(4-chloro-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3,5-difluoro-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-[2-(4-chloro-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3,5-difluoro-phenyl)-2-ethoxy-propionic acid as light yellow amporphous solid.

Workup

  1. customdescribed in example 4 d

Sources & evidence

ORD record
ord-3b310d28ff384aa99c99ad113eef190a
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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