HCID 70109284, compound → HCID 86752939, compound

HRID 1957558Notes

Reaction equation

HRID 1957558 reaction equation
C(OC([NH:11][CH:12]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:13][CH2:14][C:15]([NH:17][C@@H:18]([C:24]([O:26][CH3:27])=[O:25])[CH2:19][C:20]([O:22][CH3:23])=[O:21])=[O:16])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH:12]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:13][CH2:14][C:15]([NH:17][C@@H:18]([C:24]([O:26][CH3:27])=[O:25])[CH2:19][C:20]([O:22][CH3:23])=[O:21])=[O:16]

Participants

4

Reactant 1

HCID 70109284HCID 70109284, compound

Product 1

HCID 86752939HCID 86752939, compoundYield 104.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1.92 g (4.0 mmol) of dimethyl N-[4-(benzyloxycarbonylamino)-4-tert.-butoxycarbonylbutanoyl]-D-aspartate in 15 mL of anhydrous methanol was added 0.43 g of 10% Pd/C and the mixture was then stirred under an atmosphere of hydrogen overnight. The catalyst was removed by filtration through a Celite® pad and the filtrate concentrated in vacuo to yield 1.45 g of dimethyl N-(4-amino-4-tert.-butoxycarbonylbutanoyl)-D-aspartate as a thick clear oil. Mass Spectrum (FD+): M+1=347; IR (CHCl3, cm-1)=840, 1048, 1155, 1371, 1396, 1440, 1511, 1602, 1672, 1739, 2980, 3428, 3691; 1H NMR (30 MHz, CDCl3) δ1.51 (s, 9H), 1.66 (s, 2H), 2.07 (m, 2H), 2.46 (m, 2H), 2.85 (t, J=6.0 Hz, 2H), 3.68 (s, 3H), 3.72 (s, 3H), 3.76 (t, J=6.4 Hz, 1H), 4.78 (t, J=5.7 Hz, 1H), 7.15 (d J=8.0 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-821836f9c42b469d83e51c6202b90f1e
Source dataset
uspto-grants-1998_07
Patent number
US05786358

Reaction notes

Loading…