methyl N-{[4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexyl]carbonyl}-L-norleucinate → methyl N-{[4-(aminomethyl)cyclohexyl]carbonyl}-L-norleucinate

HRID 488656Notes

Reaction equation

HRID 488656 reaction equation
C(OC([NH:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]([C:19]([NH:21][C@H:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[O:20])[CH2:15][CH2:14]1)=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]([C:19]([NH:21][C@H:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[O:20])[CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 69803360methyl N-{[4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexyl]carbonyl}-L-norleucinate

Product 1

HCID 66920885methyl N-{[4-(aminomethyl)cyclohexyl]carbonyl}-L-norleucinate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl N-{[4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexyl]carbonyl}-L-norleucinate (830 mg, 1.98 mmol), 10% palladium on C (0.056 g) in methanol (10 mL) was stirred under an atmosphere of hydrogen for 4 hours. The mixture was filtered through diatomaceous earth and the filter cake washed with methanol (2×15 mL). The combined methanol was concentrated under reduced pressure to provide the titled compound as a colorless solid.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washthe filter cake washed with methanol (2×15 mL)
  3. concentrationThe combined methanol was concentrated under reduced pressure

Sources & evidence

ORD record
ord-007b4075ba5344d39cd1463e8a2d0912
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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