Methanesulfonyl chloride → HCID 54125536, compound

HRID 2380686Notes

Reaction equation

HRID 2380686 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C@@H:7]([CH:30]([CH3:32])[CH3:31])[C:8]([N:10]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]#[N:25])=[CH:14][CH:13]=1)=[O:9].CCN(C(C)C)C(C)C>ClCCl>[CH2:26]([N:10]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]#[N:25])=[CH:14][CH:13]=1)[C:8](=[O:9])[C@@H:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:30]([CH3:31])[CH3:32])[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 53818936HCID 53818936, compound

Product 1

HCID 54125536HCID 54125536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 0.75 g (6.5 mmol) of methanesulfonic acid chloride in 5 ml of dichloromethane is added dropwise, with stirring, to a solution of 1.8 g (5 mmol) of 2-(S)-amino-N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-3-methyl-butanoic acid amide and 1.4 ml (8 mmol) of Hunig base in 10 ml of dichloromethane. The reaction mixture is stirred at room temperature for a further 5 hours, diluted with 50 ml of dichloromethane and extracted with 20 ml of 4N hydrochloric acid. The dichloromethane phase is separated, washed in succession with water, 10 ml of bicarbonate solution and brine, dried and concentrated by evaporation to yield crude N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-2-(S)-methanesulfonylamino-3-methylbutanoic acid amide in the form of a yellowish oil of Rf value 0.56 [toluene/isopropanol/glacial acetic acid (170:30:2)]that can be used in the next step without being further purified.

Workup

  1. extractionextracted with 20 ml of 4N hydrochloric acid
  2. customThe dichloromethane phase is separated
  3. washwashed in succession with water, 10 ml of bicarbonate solution and brine
  4. customdried
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b42fc30f3c81478685162a214b87979d
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

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