Methanesulfonyl chloride → HCID 131722838, compound

HRID 651796Notes

Reaction equation

HRID 651796 reaction equation
[CH3:1][CH:2]([CH3:20])[CH2:3][CH2:4][C:5]([NH:7][N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[NH:10][C:9]1=[O:19])=[O:6].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[CH3:21][S:22]([N:16]1[CH2:15][CH2:14][C:11]2([NH:10][C:9](=[O:19])[N:8]([NH:7][C:5](=[O:6])[CH2:4][CH2:3][CH:2]([CH3:20])[CH3:1])[C:12]2=[O:13])[CH2:18][CH2:17]1)(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 131722839HCID 131722839, compound

Product 1

HCID 131722838HCID 131722838, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.514 g of 2(R)-[1(S)-tert-butoxycarbonyl)-4-phenylbutyl]-4-methyl-N-[2,4-dioxo-1,3,8-triazaspiro[4.5]decan-3-yl]valeramide in 10 ml of dry pyridine was cooled to 0° C. with stirring and 0.13 ml of methanesulphonyl chloride added. The mixture was allowed to return to room temperature and was stirred for 2 days. The solvent was evaporated and the residue partitioned between ethyl acetate and dilute hydrochloric acid. The ethyl acetate layer was washed successively with water and saturated sodium chloride solution, dried over anhydrous magnesium sulphate and the solvent evaporated. The residue was purified by flash chromatography using 5% methanol in dichloromethane for the elution. There was obtained 0.322 g of 2(R)-[1(S)-tert-butoxycarbonyl)-4-phenylbutyl]-N-[8-(methanesulphonyl)-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-3-yl]-4-methylvaleramide in the form of a white solid.

Workup

  1. customto return to room temperature
  2. stirringwas stirred for 2 days
  3. customThe solvent was evaporated
  4. customthe residue partitioned between ethyl acetate and dilute hydrochloric acid
  5. washThe ethyl acetate layer was washed successively with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customthe solvent evaporated
  8. customThe residue was purified by flash chromatography
  9. washfor the elution

Sources & evidence

ORD record
ord-436399ae7c5840baa00bc8843f868021
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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