Sulfuric Acid → Methyl ((benzyloxy)carbonyl)-L-homoserinate

HRID 12420

Reaction equation

HRID 12420 reaction equation
[O:1]=[C:2]1[C@@H:6]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5][CH2:4][O:3]1.S(=O)(=O)(O)O.[C:23](=O)([O-])[OH:24].[Na+]>CO>[CH2:10]([O:9][C:8]([NH:7][C@@H:6]([CH2:5][CH2:4][OH:3])[C:2]([O:24][CH3:23])=[O:1])=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 489185(S)-Benzyl (2-oxotetrahydrofuran-3-yl)carbamateHCID 516892Sodium Bicarbonate

Product 1

HCID 53977437Methyl ((benzyloxy)carbonyl)-L-homoserinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To the compound (500 mg) obtained in Step 1 were added methanol (5 ml) and conc. sulfuric acid (30 μl), and the mixture was stirred overnight at 60° C. To the reaction mixture was further added sodium hydrogen carbonate (250 mg), and the mixture was stirred at room temperature for 2 hrs. After celite filtration of the reaction mixture, the solvent was evaporated to give the title compound as a crude product.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hrs
  2. filtrationAfter celite filtration of the reaction mixture
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-223c89daee13463498f015655b9c9c34
Source dataset
uspto-grants-2010_06
Patent number
US07728005B2

Linked notes

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