Pyridine → HCID 19385025, compound

HRID 2399865Notes

Reaction equation

HRID 2399865 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:20])[NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[C:1]1([CH2:7][O:8][C:9]([NH:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][S:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:35])=[O:34])=[CH:17][CH:18]=2)=[O:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 46210191Benzyl 4-aminophenethylcarbamate

Product 1

HCID 19385025HCID 19385025, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 868 mg (3.22. mmol) of Cbz amine from Example 3 in 15 mL of dichloromethane was cooled to 0° C. and treated with 0.286 mL (3.54 mmol) of pyridine followed by 569 mg (0.41 mL, 3.22 mmol) of benzenesulfonyl chloride. The reaction mixture was stirred at room temperature for 2 h and then partitioned between chloroform and water. The organic phase was washed sequentially with 5% aqueous hydrochloric acid and saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated. Purification by recrystallization from ethyl acetate/hexane gave 630 mg (48%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) 7.72 (d, 2H, J=7.2 Hz), 7.48 (m, 1H), 7.39 (m, 2H), 7.33 (m, 5H), 7.02 (d, 2H, J=8.3 Hz), 6.95 (d, 2H, J=8.3 Hz), 6.55 (s, 1H), 5.06 (s, 2H), 4.68 (broad s, 1H), 3.37 (m, 2H), 2.72 (t, 2H, J=6.9 Hz). FAB MS m/z 411 (M+1).

Workup

  1. custompartitioned between chloroform and water
  2. washThe organic phase was washed sequentially with 5% aqueous hydrochloric acid and saturated aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification
  6. customby recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-00dffe1c83d54519b299c9760196174f
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

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