Methanesulfonyl chloride → HCID 86593806, compound

HRID 2052792Notes

Reaction equation

HRID 2052792 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:21][C@H:19]([OH:20])[CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])([CH3:9])([CH3:8])[CH3:7]>C(Cl)Cl>[S:2]([O:16][C:15](=[O:17])[C@@H:14]1[CH2:18][C@@H:19]([OH:20])[CH2:21][N:13]1[C:11]([O:10][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:12])([CH3:1])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 86593806HCID 86593806, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (2 eq) was slowly added at 0° C. to a DCM solution of N-(tert-butoxycarbonyl)-hydroxyproline N,O-dimethylhydroxamide and TEA (2 eq). The reaction mixture was stirred for an additional 10 minutes and allowed to attain room temperature with continued stirring for an additional 45 minutes. The solvent was then evaporated and residue taken in water. It was extracted with ethyl acetate (twice) and the combined organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated and residue dried under vacuum to give O-mesyl N-(tert-butoxycarbonyl)-hydroxyproline N,O-dimethylhydroxamide. The yield from this reaction.

Workup

  1. customto attain room temperature
  2. stirringwith continued stirring for an additional 45 minutes
  3. customThe solvent was then evaporated
  4. extractionIt was extracted with ethyl acetate (twice) and the combined organic layer
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated
  8. customresidue dried under vacuum

Sources & evidence

ORD record
ord-b067c2f186fa45adaaca11cd9a650512
Source dataset
uspto-grants-2008_02
Patent number
US07326707B2

Reaction notes

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