Toluene → Sulfamic acid 2-(methoxycarbonyl)propyl ester

HRID 327736Notes

Reaction equation

HRID 327736 reaction equation
[OH:1][CH2:2][C@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5].[S:9](=O)(=[O:18])([O:11]C1C=CC=CC=1)[NH2:10].C1(C)C=CC=CC=1>N1C=CC=CC=1>[CH3:7][O:6][C:4]([CH:3]([CH3:8])[CH2:2][O:1][S:9](=[O:18])(=[O:11])[NH2:10])=[O:5]

Participants

5

Reactant 3

HCID 1140TolueneHCID 10192563Roche ester (S)HCID 11030308Phenylsulfamate

Product 1

HCID 54337150Sulfamic acid 2-(methoxycarbonyl)propyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5.9 g (0.05 mole) of (S)-(+)methyl 3-hydroxy-2-methylpropionate, 9.5 g (0.055 mole) of phenyl sulfamate, 25 ml of toluene and 0.5 g of pyridine was heated at reflux for 2 hr. The reaction solution was concentrated under vacuum, and the residue was chromatographed, using silica gel and eluting with 2% methanol in methylene chloride. The desired fractions were concentrated under vacuum to give 3.9 g (40%) of a pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hr
  3. concentrationThe reaction solution was concentrated under vacuum
  4. customthe residue was chromatographed
  5. washeluting with 2% methanol in methylene chloride
  6. concentrationThe desired fractions were concentrated under vacuum

Sources & evidence

ORD record
ord-4050e1107da142d9af9b3d58f7c61f7f
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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