Citric Acid → N-Boc-1-amino-1-hydroxymethylcyclopropane mesylate

HRID 255466Notes

Reaction equation

HRID 255466 reaction equation
[C:1]([NH:8][C:9]1([CH2:12][OH:13])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:22]>C(N(CC)CC)C>[S:15]([OH:17])(=[O:22])(=[O:16])[CH3:14].[C:1]([NH:8][C:9]1([CH2:12][OH:13])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 31297Methanesulfonyl chlorideHCID 11286907tert-butyl N-(1-(hydroxymethyl)cyclopropyl)carbamate

Product 1

HCID 20165745N-Boc-1-amino-1-hydroxymethylcyclopropane mesylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

N-Boc-1-amino-1-hydroxymethylcyclopropane is dissolved in triethylamine under argon at 0° C. Methanesulfonyl chloride is added with a syringe and the contents stirred at room temperature overnight. The solution is poured into 10% aqueous citric acid and extracted with ethyl acetate. The organic layer is dried over MgSO4 filtered and evaporated to give N-Boc-1-amino-1-hydroxymethylcyclopropane mesylate.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ecd7527e873d456f9a2f34ed24abf4c0
Source dataset
uspto-grants-1987_10
Patent number
US04698231

Reaction notes

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