Triphenylphosphine → HCID 68618347, compound

HRID 394319Notes

Reaction equation

HRID 394319 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].[CH3:20][C:21]1[CH:22]=[C:23]([C:28]2[S:29][C:30]([CH3:36])=[C:31]([CH2:33][CH2:34]O)[N:32]=2)[CH:24]=[C:25]([CH3:27])[CH:26]=1.COC(=O)CC(=O)C(Br)C.CC1C=C(C=C(C)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][CH2:34][CH2:33][C:31]2[N:32]=[C:28]([C:23]3[CH:22]=[C:21]([CH3:20])[CH:26]=[C:25]([CH3:27])[CH:24]=3)[S:29][C:30]=2[CH3:36])=[C:9]([O:14][CH3:15])[CH:8]=1)[CH3:2]

Participants

8

Reactant 6

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 226474102-[2-(3,5-Dimethylphenyl)-5-methyl-1,3-thiazol-4-yl]ethanolHCID 226475683,5-Dimethylbenzene-1-carbothioamideHCID 22708420[Rac]-2-ethoxy-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid ethyl ester

Product 1

HCID 68618347HCID 68618347, 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-dimethyl-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-dimethyl-thiobenzamide (from 3,5-dimethyl-benzonitrile and NaSH, NH4Cl in N,N-dimethylformamide) 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-(3,5-dimethyl-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-(3,5-dimethyl-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-phenyl)-2-ethoxy-propionic acid as colorless solid.

Workup

  1. customdescribed in example 1 d

Sources & evidence

ORD record
ord-b090c8feed2e4c309cf99b2518ed673b
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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