Lithium azide → N-(1(S)-carbomethoxy-3-methylthiopropyl)3-azidomethylbenzamide

HRID 1734700Notes

Reaction equation

HRID 1734700 reaction equation
[C:1]([C@@H:5]([NH:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18]Cl)[CH:13]=1)[CH2:6][CH2:7][S:8][CH3:9])([O:3][CH3:4])=[O:2].[N-:21]=[N+:22]=[N-:23].[Li+]>CS(C)=O>[C:1]([C@@H:5]([NH:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:21]=[N+:22]=[N-:23])[CH:13]=1)[CH2:6][CH2:7][S:8][CH3:9])([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 15406276N-(1(S)-carbomethoxy-3-methylthiopropyl)3-chloromethylbenzamide

Product 1

HCID 15406277N-(1(S)-carbomethoxy-3-methylthiopropyl)3-azidomethylbenzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of the product from Step A (13.52 g, 42.80 mmol) in 50 mL of dimethylsulfoxide under nitrogen was added lithium azide (2.3 g, 47.10 mmol). The solution was stirred for 2 h. The reaction mixture was then partitioned with 300 mL of ethyl acetate and 200 mL of water. The ethyl acetate layer was washed with 125 mL of saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as an oil. 1HNMR (300 MHz, CDCl3)δ7.75 (2H, m), 7.47 (2H, m), 7.02 (1H, d, J=8 Hz), 4.94 (1H, q, J=5 Hz), 4.41 (2H, s), 3.80 (3H, s), 2.60 (2H, t, J=6 Hz), 2.30 (1H, m), 2.15 (1H, m), 2.11 (3H, s).

Workup

  1. customThe reaction mixture was then partitioned with 300 mL of ethyl acetate and 200 mL of water
  2. washThe ethyl acetate layer was washed with 125 mL of saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6359b9049344b49a7375f24f8ffb628
Source dataset
uspto-grants-1996_07
Patent number
US05534537

Reaction notes

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