Water → (S)-Benzyl (2-oxotetrahydrofuran-3-yl)carbamate

HRID 12419

Reaction equation

HRID 12419 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4]O.C(=O)([O-])O.[Na+].O.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(OCC)(=O)C.CCOCC>[O:8]=[C:6]1[C@@H:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:3][CH2:4][O:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 12647L-HomoserineHCID 516892Sodium Bicarbonate

Product 1

HCID 489185(S)-Benzyl (2-oxotetrahydrofuran-3-yl)carbamate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To L-homoserine (2 g) were added sodium hydrogen carbonate (3.7 g) and water (30 ml), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were further added benzyl chloroformate (3.9 ml) and ether (10 ml), and the mixture was stirred at room temperature for 18 hrs. The reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give the title compound (2.5 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hrs
  2. washwashed with 1N hydrochloric acid
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe obtained crude product
  6. customwas purified by silica gel chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-85ad0931441546fdb77303f6acdb74a0
Source dataset
uspto-grants-2010_06
Patent number
US07728005B2

Linked notes

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