Benzyl Alcohol → benzyl (2S)-3-amino-2-hydroxypropanoate hydrochloride

HRID 1587980Notes

Reaction equation

HRID 1587980 reaction equation
S(Cl)([Cl:3])=O.COC1C=CC(COC([NH:15][CH2:16][C@@H:17]([C:19](O)=[O:20])[OH:18])=O)=CC=1.C(OCC)C.[CH2:29]([OH:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[ClH:3].[CH2:29]([O:36][C:19](=[O:20])[C@@H:17]([OH:18])[CH2:16][NH2:15])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 127738164-methoxybenzyloxycarbonyl-(S)-isoserine

Product 1

HCID 131717979benzyl (2S)-3-amino-2-hydroxypropanoate hydrochloride

Procedure

At 0°-5°, add thionyl chloride (11.0 ml) dropwise to N-(4-methoxybenzyloxycarbonyl)-(S)-isoserine (10.0 g) in benzyl alcohol (100 ml), warm the mixture to room temperature, and stir for 20 hours. 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, a tan solid, m.p. 127°-130° C., [α]D26 =-18.6° (MeOH).

Workup

  1. filtrationfilter the solid
  2. washWash the solid with diethyl ether
  3. customdry in vacuo

Sources & evidence

ORD record
ord-3ce38b5ade5441a9b65647254ef6b6fb
Source dataset
uspto-grants-1993_06
Patent number
US05219886

Reaction notes

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