2,4-Imidazolidinedione, 3-(hydroxymethyl)-1-(2-propynyl)- → [3-propargyl-2,5-dioxo-imidazolidinyl]-methyl (1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylate

HRID 1719752Notes

Reaction equation

HRID 1719752 reaction equation
[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:14])[O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[C@H:3]1[C:15]([OH:17])=[O:16].[CH2:19]([N:22]1[CH2:26][C:25](=[O:27])[N:24]([CH2:28]O)[C:23]1=[O:30])[C:20]#[CH:21]>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:14])[O:8][CH2:9][C:10]([F:13])([F:11])[F:12])[C@H:3]1[C:15]([O:17][CH2:28][N:24]1[C:25](=[O:27])[CH2:26][N:22]([CH2:19][C:20]#[CH:21])[C:23]1=[O:30])=[O:16]

Participants

4

Reactant 2

HCID 117895972,4-Imidazolidinedione, 3-(hydroxymethyl)-1-(2-propynyl)-HCID 13390085(1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid

Product 1

HCID 13188358[3-propargyl-2,5-dioxo-imidazolidinyl]-methyl (1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Using the procedure of Step F of Example 9, the acid of Step D of Example 1 and (3-propargyl-2,5-dioxo-imidazolidinyl)-methanol were reacted to obtain [3-propargyl-2,5-dioxo-imidazolidinyl]-methyl (1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =-4°±1° (c=1% in benzene).

Sources & evidence

ORD record
ord-efe728005de24df8bb8759403e011ad8
Source dataset
uspto-grants-1985_09
Patent number
US04542142

Reaction notes

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