Hydrogen Peroxide → HCID 11425582, compound

HRID 1277410Notes

Reaction equation

HRID 1277410 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[OH:17]O>C(#N)C.[Pd]>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5]([CH3:6])=[O:17]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 111051N-(tert-Butyloxycarbonyl)-D-methionine

Product 1

HCID 11425582HCID 11425582, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

In 200 ml of acetonitrile is dissolved 37 g of BOC-(D)-Met-OH, followed by adding 19 ml of a 30% aqueous solution of hydrogen peroxide, and the mixture is stirred for 8 hours at room temperature. Palladium black is added to the reaction mixture, and then the mixture is stirred for one hour. Palladium black is filtered off, and then acetonitrile is distilled off. The residue is extracted with 300 ml of n-butanol. The n-butanol layer is washed with aqueous solution of NaCl, and then n-butanol is distilled off. The residue is recrystallized from diethyl ether and, then,AcOEt-diethyl ether to give 32 g of crystals, m.p. 125°-126° C., [α]D23 +7.2° (C=0.5, DMF), Rf1 =0.27.

Workup

  1. stirringthe mixture is stirred for one hour
  2. filtrationPalladium black is filtered off
  3. distillationacetonitrile is distilled off
  4. extractionThe residue is extracted with 300 ml of n-butanol
  5. washThe n-butanol layer is washed with aqueous solution of NaCl
  6. distillationn-butanol is distilled off
  7. customThe residue is recrystallized from diethyl ether and, then,AcOEt-diethyl ether

Sources & evidence

ORD record
ord-a6c266d05e244f5a85b29475b14a8c89
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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