trans-4-azido-N-tert-butoxycarbonyl-L-proline 3-quinolylamide → trans-4-Amino-N-tert-Butoxycarbonyl-L-Proline 3-Quinolylamide

HRID 2185402Notes

Reaction equation

HRID 2185402 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:28])[C@@H:13]2[CH2:17][C@@H:16]([N:18]=[N+]=[N-])[CH2:15][N:14]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:2]=1>[Pd].CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:28])[C@@H:13]2[CH2:17][C@@H:16]([NH2:18])[CH2:15][N:14]2[C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH:2]=1

Participants

4

Reactant 1

HCID 131723249trans-4-azido-N-tert-butoxycarbonyl-L-proline 3-quinolylamide

Product 1

HCID 70173042trans-4-Amino-N-tert-Butoxycarbonyl-L-Proline 3-QuinolylamideYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of trans-4-azido-N-tert-butoxycarbonyl-L-proline 3-quinolylamide (D, 526 mg) and 10% palladium on activated carbon (102 mg) in methanol (15 mL) was stirred at room temperature for 4 hr under hydrogen. The catalysts were removed by filtration and washed with methanol. The combined organic layers were evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1 to 5: 1, v/v) to afford the title compound (477 mg) as a colorless sticky oil.

Workup

  1. customThe catalysts were removed by filtration
  2. washwashed with methanol
  3. customThe combined organic layers were evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record
ord-a3c706b5840843039a0135b9be192c7b
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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