Diethyl Carbonate → HCID 19956142, compound

HRID 1779686Notes

Reaction equation

HRID 1779686 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][C@@H:12]([CH2:14]N3CCN(C(C(OCC4C=CC=CC=4)=O)CC(OCC4C=CC=CC=4)=O)CC3)[O:11][C:10]2=[O:43])=[CH:5][CH:4]=1.ClCC1C=CC(N)=CC=1.[O:53]1CC1CO.ClC1C=CC(NCC(O)CO)=C(C)C=1.C(=O)(OCC)OCC.CC(C)([O-])C>>[Cl:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:13][CH:12]([CH2:14][OH:53])[O:11][C:10]2=[O:43])=[CH:7][CH:8]=1

Participants

7

Reactant 6

HCID 7766Diethyl CarbonateHCID 11164GlycidolHCID 45749132-Methylpropan-2-olateHCID 113209864-ChloromethylanilineHCID 19956146HCID 19956146, compoundHCID 57206257HCID 57206257, compound

Product 1

HCID 19956142HCID 19956142, compound

Procedure

1.1 g of 3-(4-chloromethylphenyl)-5(R)-[4-(1,2di-benzyloxycarbonylethyl)piperazinomethyl]oxazolidin-2-one [obtainable by reaction of 4-chloromethylaniline with 2,3-epoxypropan-1-ol to give N-(4-chloro-methylphenyl)-2,3-dihydroxypropylamine, reaction with diethyl carbonate in the presence of K tert-butoxide to give 3-(4-chloromethylphenyl)-5-hydroxymethyl-oxazolidin-2-one, subsequent esterification with methanesulfonyl chloride and reaction with 1-(1,2-dibenzyloxycarbonylethyl)piperazine], dissolved in 30 ml of DMF, are treated at room temperature with 0.9 g of freshly prepared guanidine, dissolved in 10 ml of DMF, and the mixture is stirred for two hours. After removal of the solvent and customary working up, 3-(4-guanidinylmethylphenyl)-5(R)-[4-(1,2-dibenzyloxycarbonylethyl)piperazinomethyl]oxazolidin-2-one is obtained.

Workup

  1. customto give

Sources & evidence

ORD record
ord-aa2ded82cbb3498db8dfb8524ad070dc
Source dataset
uspto-grants-1997_05
Patent number
US05627197

Reaction notes

Loading…