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-difluoroethoxy)-1-propenyl]-cyclopropane-carboxylate

HRID 1639438Notes

Reaction equation

HRID 1639438 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:4](/[CH:5]=[CH:6]\[C:7](=[O:13])[O:8][CH2:9][CH:10]([F:12])[F:11])[CH:3]1[C:14]([OH:16])=[O:15].[CH2:18]([N:21]1[CH2:25][C:24](=[O:26])[N:23]([CH2:27]O)[C:22]1=[O:29])[C:19]#[CH:20]>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:17])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:13])[O:8][CH2:9][CH:10]([F:11])[F:12])[C@H:3]1[C:14]([O:16][CH2:27][N:23]1[C:24](=[O:26])[CH2:25][N:21]([CH2:18][C:19]#[CH:20])[C:22]1=[O:29])=[O:15]

Participants

4

Reactant 2

HCID 117895972,4-Imidazolidinedione, 3-(hydroxymethyl)-1-(2-propynyl)-HCID 867435342,2-dimethyl-3-[(Z) 3-oxo-3-(2,2-difluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid

Product 1

HCID 131716202[3-propargyl-2,5-dioxo-imidazolidinyl]-methyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-(2,2-difluoroethoxy)-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-(2,2-difluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid 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-difluoroethoxy-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+18°±2° (c=1% in CHCl3).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ecb4e4519e074e73bc4de1083daa84d1
Source dataset
uspto-grants-1989_11
Patent number
US04883806

Reaction notes

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