Triphenylphosphine → HCID 68617930, compound

HRID 394301Notes

Reaction equation

HRID 394301 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(OC(CC1C=CC(O[CH2:34][C:35]2[N:36]=[C:37]([C:40]3[CH:45]=[CH:44][C:43]([CH:46]([CH3:48])[CH3:47])=[CH:42][CH:41]=3)[S:38][CH:39]=2)=C(C)C=1)C(O)=O)C.[C:50]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(O)C>[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][CH2:50][CH2:34][C:35]2[N:36]=[C:37]([C:40]3[CH:41]=[CH:42][C:43]([CH:46]([CH3:47])[CH3:48])=[CH:44][CH:45]=3)[S:38][CH:39]=2)=[C:9]([F:14])[CH:8]=1)[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10388498HCID 10388498, compoundHCID 68618019[Rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester

Product 1

HCID 68617930HCID 68617930, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 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 2-2-(4-isopropyl-phenyl)-thiazol-4-yl]-ethanol (prepared from 4-chloromethyl-2-(4-isopropyl-phenyl)-thiazole (example 5) according to the sequence described in examples 13 a]to d]) in tetrahydrofuran in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-2-ethoxy-3-(3-fluoro-4-{2-[2-(4-isopropyl-phenyl)-thiazol-4-yl]-ethoxy}-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-(3-fluoro-4-{2-[2-(4-isopropyl-phenyl)-thiazol-4-yl)-ethoxy}-phenyl)-propionic acid as light yellow solid.

Workup

  1. customdescribed in example 1 d

Sources & evidence

ORD record
ord-ee3341a8b62443e8933917be8264bc94
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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