HCID 40592955, compound → HCID 13190105, compound

HRID 1164379Notes

Reaction equation

HRID 1164379 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([NH:15][C@@H:16]([C:29](=[O:31])[NH2:30])[CH2:17][CH2:18][C:19]([O:21]CC1C=CC=CC=1)=[O:20])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([NH:15][C@@H:16]([C:29](=[O:31])[NH2:30])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 40592955HCID 40592955, compound

Product 1

HCID 13190105HCID 13190105, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl t-butyloxycarbonyl-L-valyl-D-isoglutaminate (7.5 g, 17.2 mmol) was catalytically hydrogenated in methanol (150 ml) using palladium black as a catalyst at room temperature for 6 hours. The catalyst was filtered and the solvent was evaporated. Petroleum ether was added to the residue. After trituration, the resulting powder was filtered. Reprecipitation from ethyl acetate/petroleum ether gave t-butyloxycarbonyl-L-valyl-D-isoglutamine (6.0 g). m.p. 89°-90° C. (dec.). [α]D23 +9.46° (C 0.5, DMF). Rf2 =0.32.

Workup

  1. customat room temperature
  2. customfor 6 hours
  3. filtrationThe catalyst was filtered
  4. customthe solvent was evaporated
  5. additionPetroleum ether was added to the residue
  6. filtrationAfter trituration, the resulting powder was filtered
  7. customReprecipitation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-13ceb9e711ee4d45966ee089e402e85c
Source dataset
uspto-grants-1983_01
Patent number
US04369178

Reaction notes

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