HCID 18664136, compound → HCID 18664135, compound

HRID 1957559Notes

Reaction equation

HRID 1957559 reaction equation
C(OC([NH:11][CH:12]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:13][CH2:14][C:15]([NH:17][C@@H:18]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:16])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][CH:12]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:13][CH2:14][C:15]([NH:17][C@@H:18]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:16]

Participants

4

Reactant 1

HCID 18664136HCID 18664136, compound

Product 1

HCID 18664135HCID 18664135, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3.12 g (5.9 mmol) of diethyl N-[4-(benzyloxycarbonylamino)-4-tert.-butoxycarbonylbutanoyl]-D-glutamate in 27 mL of anhydrous ethanol was added 0.66 g of 10% Pd/C. The reaction mixture was then stirred under an atmosphere of hydrogen overnight. The catalyst was removed by filtration through Celite® and the filtrate was concentrated in vacuo to give 1.83 g (81%) of diethyl N-(4-amino-4-tert.-butoxycarbonylbutanoyl)-D-glutamate as a white gum. Mass Spectrum (FD+): M+1=389; IR (CHCl3, cm-1)=845, 1023, 1156, 1370, 1394, 1448, 1477, 1507, 1602, 1673, 1729, 2983, 3024, 3426, 3690; Anal. Calcd. for C18H32N2O7 : C, 55.66; H, 8.30; N, 7.21.; Found: C, 55.93; H, 8.01; N, 7.26; 1H NMR (300 MHz, CDCl3) δ1.22-1.30 (m, 6H), 1.45 (s, 9H), 1.75-1.84 (m, 2H), 1.96-2.02 (m, 2H), 2.14-2.22 (m, 2H), 2.32-2.43 (m, 4H), 4.09-4.22 (m, 5H), 4.58-4.60 (m, 1H), 6.96 (d, J=7.4 Hz, 1H).

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-12cf76e418b74181bdaebcdd91d7e48d
Source dataset
uspto-grants-1998_07
Patent number
US05786358

Reaction notes

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