Methanesulfonyl chloride → HCID 70223394, compound

HRID 1531554Notes

Reaction equation

HRID 1531554 reaction equation
[C:1]([O:5][C:6](=[O:45])[N:7]([CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([N+:34]([O-:36])=[O:35])[CH:32]=2)[NH:27][C:26]=1[C:37]1[CH:42]=[C:41]([CH3:43])[CH:40]=[C:39]([CH3:44])[CH:38]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18]S(C)(=O)=O)=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:46][S:47](Cl)(=[O:49])=[O:48]>C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:45])[N:7]([CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([N+:34]([O-:36])=[O:35])[CH:32]=2)[NH:27][C:26]=1[C:37]1[CH:38]=[C:39]([CH3:44])[CH:40]=[C:41]([CH3:43])[CH:42]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[C:16]([S:47]([CH3:46])(=[O:49])=[O:48])[C:17]=1[S:47]([CH3:46])(=[O:49])=[O:48])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 54430957HCID 54430957, compound

Product 1

HCID 70223394HCID 70223394, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of {2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethyl}-[4-(4-methanesulfonylaminophenyl)butyl]carbamic acid tert-butyl ester (300 mg in 7 mL methylene chloride) at 0° C. was added 0.135 mL triethylamine and 0.066 mL methanesulfonyl chloride and the mixture sired at low temperature. After 30 minutes, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate and partitioned between water and ethyl acetate. The organic portion was washed successively with saturated ammonium chloride, saturated sodium bicarbonate and brine, then dried over sodium sulfate and concentrated in vacuo to give the crude title compound (330 mg).

Workup

  1. customthe reaction was quenched by the addition of saturated aqueous sodium bicarbonate
  2. custompartitioned between water and ethyl acetate
  3. washThe organic portion was washed successively with saturated ammonium chloride, saturated sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0078c30df14342ed8046e3ca6b49f495
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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