Methanesulfonyl chloride → HCID 54418214, compound

HRID 1934700Notes

Reaction equation

HRID 1934700 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:23][C@@H:24]([CH3:27])[CH2:25][OH:26])=[C:7]([CH:22]=1)[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)=[O:9])#[N:2].[CH3:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:23][C@@H:24]([CH3:27])[CH2:25][O:26][S:29]([CH3:28])(=[O:31])=[O:30])=[C:7]([CH:22]=1)[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)=[O:9])#[N:2]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 54513542HCID 54513542, compound

Product 1

HCID 54418214HCID 54418214, compoundYield 112.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-5-cyano-N-(3,4-dimethoxybenzyl)-2-(2-hydroxy-1-methylethylamino)benzamide (4 g) in pyridine (20 mL) was added methanesulfonyl chloride (1.36 g), and the mixture was stirred for an hour at 0° C. The resulting mixture was diluted with ethyl acetate and washed successively with water and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give (S)-5-cyano-N-(3,4-dimethoxybenzyl)-2-[2-(methanesulfonyloxy)-1-methylethylamino]benzamide (5.43 g) as an oil.

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-888422b5b82b4e4d9a7ac27aa7bbeafc
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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