Ethanol → (S)-isoserine ethyl ester hydrochloride

HRID 1587981Notes

Reaction equation

HRID 1587981 reaction equation
S(Cl)([Cl:3])=O.COC1C=CC(COC([NH:15][CH2:16][C@@H:17]([C:19]([OH:21])=[O:20])[OH:18])=O)=CC=1.[CH2:24](O)[CH3:25]>>[ClH:3].[CH2:24]([O:21][C:19](=[O:20])[C@@H:17]([OH:18])[CH2:16][NH2:15])[CH3:25]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 127738164-methoxybenzyloxycarbonyl-(S)-isoserine

Product 1

HCID 86746976(S)-isoserine ethyl ester hydrochloride

Procedure

At 0°-5°, add thionyl chloride (2.80 ml) dropwise to N-(4-methoxybenzyloxycarbonyl)-(S)-isoserine (5.0 g) in absolute ethanol (100 ml). Heat the mixture under reflux for 1 hour and stir for 20 hours at room temperature. Concentrate the reaction mixture in vacuo and pour the reaction mixture into diethyl ether (300 ml), and filter the solid. Wash the solid with diethyl ether and dry in vacuo to give the title compound, an amber oil, [α]D26 =-19.8° (MeOH).

Workup

  1. temperatureHeat the mixture
  2. temperatureunder reflux for 1 hour
  3. concentrationConcentrate the reaction mixture in vacuo
  4. additionpour the reaction mixture into diethyl ether (300 ml)
  5. filtrationfilter the solid
  6. washWash the solid with diethyl ether
  7. customdry in vacuo

Sources & evidence

ORD record
ord-61d0b6dc72a04ba68549abe8b776d6d3
Source dataset
uspto-grants-1993_06
Patent number
US05219886

Reaction notes

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