p-Toluenesulfonic acid monohydrate → HCID 86601015, compound

HRID 1796790Notes

Reaction equation

HRID 1796790 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]([OH:17])([CH3:16])[CH:14]=[CH2:15])[CH2:11][O:10]C1(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(=O)(O)[O-].[Na+]>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:12]([CH2:11][OH:10])[C:13]([OH:17])([CH3:16])[CH:14]=[CH2:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 69597644HCID 69597644, compound2×

Product 1

HCID 86601015HCID 86601015, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4-(1-hydroxy-1-methyl-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (compound of formula II, 3.3 g, 12.1 mmol, prepared as in Ageno, G.; Banfi, L.; Cascio, G.; Guanti, G.; Manghisi, E.; Riva, R.; Rocca, V. Tetrahedron, 1995, 29, 8121) in 100 ml of methanol was added p-toluenesulfonic acid monohydrate (0.215 g, 1.1 mmol). After stirring for about 30 minutes at a temperature of about 20° C. to about 25° C., the mixture was diluted with saturated aqueous sodium bicarbonate and was concentrated in vacuo. The residue was diluted with water and was extracted 3 times into ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford 2.8 g of (2-Hydroxy-1-hydroxymethyl-2-methyl-but-3-enyl)-carbamic acid tert-butyl ester (compound of formula III) as a colorless syrup.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionwas extracted 3 times into ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-07c49dade76f4be583598c8180f574e2
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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