Glycidol → HCID 136125521, compound

HRID 1281751Notes

Reaction equation

HRID 1281751 reaction equation
[C:1]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][CH:21]([CH2:23][O:24]S(C)(=O)=O)[O:20]C2=O)=[CH:14][CH:13]=1)=[NH:11])(=[O:8])C1C=CC=CC=1.[O:30]=C1ON=C(C2C=CC(N)=CC=2)N1.O1CC1CO>>[O:30]=[C:1]1[O:8][N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:22][CH:21]([OH:20])[CH2:23][OH:24])=[CH:14][CH:13]=2)[NH:9]1

Participants

4

Reactant 3

HCID 11164GlycidolHCID 1354531853-(4-Aminophenyl)-1,2,4-oxadiazol-5(2H)-oneHCID 140440993HCID 140440993, compound

Product 1

HCID 136125521HCID 136125521, compound

Procedure

3.0 g of 3-[4-(N-benzoylamidino)phenyl]-5-methanesulfonyloxymethyl-2-oxazolidinone [obtainable by reacting 4-(5-oxo-1,2,4-oxadiazolin-3-yl)aniline with 2,3-epoxypropan-1-ol to give N-[4-(5-oxo-1,2,4-oxadiazolin-3-yl)phenyl]-2,3-dihydroxypropylamine, reacting with diethyl carbonate in the presence of tert-butoxide to give 3-[4-(5-oxo-1,2,4-oxazolin-3-yl)phenyl]-5-hydroxymethyl-2-oxazolidinone, reductive cleavage of the 5-oxo-1,2,4-oxadiazoline group, reacting with benzoyl chloride and subsequently esterifying with methanesulfonyl chloride) dissolved in 10 ml of DMF, are added to a solution of 1.2 g of 4-ethoxycarbonylmethylpiperazine (“A”) in 20 ml of DMF, and the mixture is stirred at room temperature for 60 min. Removal of the solvent and the usual working up result in 3-[4-(N-benzoylamidino)phenyl]-5-(4-ethoxycarbonylmethylpiperazinomethyl)-2-oxazolidinone, m.p. 114°.

Sources & evidence

ORD record
ord-11f74c65517745fcb5e2e31e80fa1796
Source dataset
uspto-grants-2002_09
Patent number
US06455529B1

Reaction notes

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