Hydrogen Peroxide → BOC-Tyr-(D)-Met(O)-Gly-OH

HRID 1277395Notes

Reaction equation

HRID 1277395 reaction equation
[NH:1]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:2]([C:11]([NH:13][C@@H:14]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])[CH2:15][CH2:16][S:17][CH3:18])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.OO.CN(C=[O:39])C>CO.C(O)(=O)C.[Pd]>[NH:1]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:2]([C:11]([NH:13][C@@H:14]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])[CH2:15][CH2:16][S:17]([CH3:18])=[O:39])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 6228DimethylformamideHCID 12919645N-(tert-Butoxycarbonyl)-L-tyrosyl-D-methionylglycine

Product 1

HCID 12919648BOC-Tyr-(D)-Met(O)-Gly-OH

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

In a mixed solvent comprising 10 ml of MeOH and 5 ml of acetic acid is dissolved 2.2 g of BOC-Tyr-(D)-Met-Gly-OH, followed by adding 0.6 ml of 30% aqueous hydrogen peroxide solution, and the mixture is stirred at roomtemperature for 5 hours. Following the addition of a small amount of palladium black, the mixture is stirred. The catalyst is filtered out, andthe solvent is distilled off, whereby the precipitated crystals are collected by filtration. Thus obtained is 2.1 g of the desired product, m.p. 185° C. (decomposed), Rf1 =0.20, [α]D21 +1.8° (c=0.5, DMF)

Workup

  1. stirringthe mixture is stirred
  2. filtrationThe catalyst is filtered out
  3. distillationandthe solvent is distilled off
  4. filtrationwhereby the precipitated crystals are collected by filtration
  5. customThus obtained

Sources & evidence

ORD record
ord-18cf99727005470b972861d354daf2ae
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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