Triphenylphosphine → HCID 68616084, compound

HRID 394298Notes

Reaction equation

HRID 394298 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]([CH3:13])[C:10]([OH:14])=[C:9]([CH3:15])[CH:8]=1)[CH3:2].[CH:20]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[S:30][C:31]([CH3:37])=[C:32]([CH2:34][CH2:35]O)[N:33]=2)=[CH:25][CH:24]=1)([CH3:22])[CH3:21].COC(=O)CC(=O)C(Br)C.C(C1C=CC(C(N)=S)=CC=1)(C)C.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]([CH3:15])[C:10]([O:14][CH2:35][CH2:34][C:32]2[N:33]=[C:29]([C:26]3[CH:25]=[CH:24][C:23]([CH:20]([CH3:21])[CH3:22])=[CH:28][CH:27]=3)[S:30][C:31]=2[CH3:37])=[C:11]([CH3:13])[CH:12]=1)[CH3:2]

Participants

8

Reactant 6

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 20788314-(Propan-2-yl)benzene-1-carbothioamideHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 226474402-[2-(4-Isopropyl-phenyl)-5-methyl-thiazol-4-yl]-ethanolHCID 68617953[Rac]-2-ethoxy-3-(4-hydroxy-3,5-dimethyl-phenyl)-propionic acid ethyl ester

Product 1

HCID 68616084HCID 68616084, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to the procedure described in example 1 d], [rac]-2-ethoxy-3-(4-hydroxy-3,5-dimethyl-phenyl)-propionic acid ethyl ester (example 45 a]) was reacted with 2-[2-(4-isopropyl-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-isopropyl-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]-2-ethoxy-3-(4-{2-[2-(4-isopropyl-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3,5-dimethyl-phenyl)-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 4 e], to yield [rac]-2-ethoxy-3-(4-{2-[2-(4-isopropyl-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3,5-dimethyl-phenyl)-propionic acid as yellow amorphous solid.

Workup

  1. customdescribed in example 1 d

Sources & evidence

ORD record
ord-0221a76a6bd6432e90a35b9d1fe86136
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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