N-(1(S)-carbomethoxy-3-methylthiopropyl)3-azidomethylbenzamide → N-(1(S)-carbomethoxy-3-methylthiopropyl)3-aminomethylbenzamide

HRID 1901587Notes

Reaction equation

HRID 1901587 reaction equation
[C:1]([C@@H:5]([NH:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]=[N+]=[N-])[CH:13]=1)[CH2:6][CH2:7][S:8][CH3:9])([O:3][CH3:4])=[O:2].[H][H]>CO.[Pd]>[C:1]([C@@H:5]([NH:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH2:19])[CH:13]=1)[CH2:6][CH2:7][S:8][CH3:9])([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 15406277N-(1(S)-carbomethoxy-3-methylthiopropyl)3-azidomethylbenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 15406278N-(1(S)-carbomethoxy-3-methylthiopropyl)3-aminomethylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product from Step B (11.8 g, 35.08 mmol) in 150 mL of methanol under nitrogen was added 1.5 g 10% palladium on carbon. Hydrogen was applied to the mixture at 1 atmosphere for 1.5 h. The reaction mixture was filtered and concentrated in vacuo to obtain 10.3 g (34.76 mmol) of crude product as an oil. The crude product was chromatographed on 500 g of silica gel with chloroform/methanol 95/5 as eluant to afford the title compound as an oil. 1HNMR (300 MHz, CDCl3)δ 7.78 (1H, s), 7.68 (1H, d, J=7 Hz), 7.47 (1H, d, J=7 Hz), 7.40 (1H, t, J=8 Hz), 7.02 (1H, d, J=7 Hz), 4.93 (1H, q, J=5 Hz), 3.92 (2H, s), 3.79 (3H, s), 2.59 (2H, t, J=8 Hz), 2.24 (1H, m), 2.12 (1H, m), 2.10 (3H, s), 1.85 (2H,s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto obtain 10.3 g (34.76 mmol) of crude product as an oil
  4. customThe crude product was chromatographed on 500 g of silica gel with chloroform/methanol 95/5 as eluant

Sources & evidence

ORD record
ord-78ca7ddb46cc41feb91429ddab416a08
Source dataset
uspto-grants-1996_11
Patent number
US05578629

Reaction notes

Loading…