N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-alpha-aspartyl]-O-tert-butyl-L-alpha-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucine benzyl ester → L-Leucine

HRID 635628Notes

Reaction equation

HRID 635628 reaction equation
C([O:8][C:9](=[O:72])[C@H:10]([CH2:68][CH:69]([CH3:71])[CH3:70])[NH:11]C(=O)[C@H](C(C)(C)C)NC(=O)[C@H](CC1C=CC=CC=1C)NC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)[C@H](CC(=O)OC(C)(C)C)NC(=O)CCC(OC(C)(C)C)=O)C1C=CC=CC=1>CN(C)C=O.[Pd]>[NH2:11][C@H:10]([C:9]([OH:72])=[O:8])[CH2:68][CH:69]([CH3:71])[CH3:70]

Participants

4

Reactant 1

HCID 22942120N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-alpha-aspartyl]-O-tert-butyl-L-alpha-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucine benzyl ester

Product 1

HCID 6106L-Leucine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 6.8 g (6.75 mmol) of N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucine benzyl ester in 200 ml of dimethylformamide was hydrogenated over 600 mg of 10% palladium/carbon for 1 hour. The catalyst was removed by filtration and the filtrate was evaporated to give 15 g of crude product which was chromatographed on silica gel using 10-15% methanol in dichloromethane for the elution to give 6 g of N-N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucine as a white solid of melting point 235-236° C.; MS: m/e 918.4 [M+H]+, m/e 940.3 [M+Na]+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customto give 15 g of crude product which
  4. customwas chromatographed on silica gel using 10-15% methanol in dichloromethane for the elution

Sources & evidence

ORD record
ord-28b6cc5461d145c8b3b9180a7e79036d
Source dataset
uspto-grants-2001_02
Patent number
US06187905B1

Reaction notes

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