Triphenylphosphine → HCID 68617741, compound

HRID 394316Notes

Reaction equation

HRID 394316 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]=[CH:11][C:10]([OH:13])=[C:9]([O:14][CH3:15])[CH:8]=1)[CH3:2].CO[C:22]1[CH:23]=[C:24]([C:30]2[S:31][C:32]([CH3:38])=[C:33]([CH2:35][CH2:36]O)[N:34]=2)[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1.[CH3:39][O:40]C(=O)CC(=O)C(Br)C.COC1C=C(C=C(OC)C=1)C(N)=S.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:12]=[CH:11][C:10]([O:13][CH2:36][CH2:35][C:33]2[N:34]=[C:30]([C:24]3[CH:23]=[CH:22][C:27]([O:40][CH3:39])=[C:26]([O:28][CH3:29])[CH:25]=3)[S:31][C:32]=2[CH3:38])=[C:9]([O:14][CH3:15])[CH:8]=1)[CH3:2]

Participants

8

Reactant 6

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27584913,5-DimethoxythiobenzamideHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 226474532-[2-(3,5-Dimethoxy-phenyl)-5-methyl-thiazol-4-yl)-ethanolHCID 22708420[Rac]-2-ethoxy-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid ethyl ester

Product 1

HCID 68617741HCID 68617741, 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-methoxy-phenyl)-propionic acid ethyl ester [example 48 a]) was reacted with 2-[2-(3,5-dimethoxy-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 3,5-dimethoxy-thiobenzamide [PCT Int. Appl. (1992), WO 92/09586 A1] 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-(3,4-dimethoxy-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-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-(3,4-dimethoxy-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-phenyl)-2-ethoxy-propionic acid as light yellow solid.

Workup

  1. customdescribed in example 1 d

Sources & evidence

ORD record
ord-846dca7dc7ef4e949c350cb1be9cfaf5
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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