2-Fluoroethanol → (3-propargyl-2,5-dioxo-1-imidazolidinyl)-methyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-(2-fluoroethoxy)-1-propenyl]-cyclopropane-carboxylate

HRID 1719750Notes

Reaction equation

HRID 1719750 reaction equation
[CH3:1][C:2]1([CH3:16])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:12])[O:8][CH2:9][CH2:10][F:11])[C@H:3]1[C:13]([OH:15])=[O:14].FCCO.[CH2:21]([N:24]1[CH2:28][C:27](=[O:29])[N:26]([CH2:30]O)[C:25]1=[O:32])[C:22]#[CH:23]>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:16])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:12])[O:8][CH2:9][CH2:10][F:11])[C@H:3]1[C:13]([O:15][CH2:30][N:26]1[C:27](=[O:29])[CH2:28][N:24]([CH2:21][C:22]#[CH:23])[C:25]1=[O:32])=[O:14]

Participants

5

Reactant 3

HCID 97372-FluoroethanolHCID 117895972,4-Imidazolidinedione, 3-(hydroxymethyl)-1-(2-propynyl)-HCID 86740321(1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2-fluoroethoxy)-1-propenyl]cyclopropane-carboxylic acid

Product 1

HCID 86740320(3-propargyl-2,5-dioxo-1-imidazolidinyl)-methyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-(2-fluoroethoxy)-1-propenyl]-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Step F of Example 9, (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-(2-fluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid prepared as in Example 21 except 2-fluoroethanol was used and (3-propargyl-2,5-dioxo-imidazolidinyl)-methanol were reacted to obtain (3-propargyl-2,5-dioxo-1-imidazolidinyl)-methyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-(2-fluoroethoxy)-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+18°±2° (c=1% in CHCl3)

Sources & evidence

ORD record
ord-7897c2c1ac514c7b834e618ba19034e3
Source dataset
uspto-grants-1985_09
Patent number
US04542142

Reaction notes

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