Triphenylphosphine → HCID 68617614, compound

HRID 394302Notes

Reaction equation

HRID 394302 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:19]1([CH3:33])[CH:24]=[CH:23][C:22]([C:25]2[S:26][CH:27]=[C:28]([CH2:30][CH2:31]O)[N:29]=2)=[CH:21][CH:20]=1.C(OC(=O)CC1N=C(C2C=CC(C)=CC=2)SC=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].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:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:31][CH2:30][C:28]2[N:29]=[C:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:33])=[CH:20][CH:21]=3)[S:26][CH:27]=2)=[C:9]([F:14])[CH:8]=1)[CH3:2]

Participants

8

Reactant 6

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 20110334HCID 20110334, compoundHCID 21226445Aluminium lithium hydrideHCID 22647515HCID 22647515, compoundHCID 68618019[Rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester

Product 1

HCID 68617614HCID 68617614, compound

Reagents, catalysts & solvents 1

HCID 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-p-tolyl-thiazol-4-yl)-ethanol (prepared from (2-p-tolyl-thiazol-4-yl)-acetic acid ethyl ester [Collection of Czechoslovak Chemical Communications (2001), 66(12), 1809-1830] with lithium aluminium hydride in analogy to the procedure described in example 12 b]) in tetrahydrofuran in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-2-ethoxy-3-{3-fluoro-4-[2-(2-p-tolyl-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-fluoro-4-[2-(2-p-tolyl-thiazol-4-yl)-ethoxy)-phenyl}-propionic acid as light yellow solid.

Workup

  1. customdescribed in example 1 d

Sources & evidence

ORD record
ord-397dd8414f1046a6a05b91b342101ec9
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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