Citric Acid → Methanesulfonic acid 2-tert-butoxycarbonylamino-2-methyl-propyl ester

HRID 255464Notes

Reaction equation

HRID 255464 reaction equation
[C:1]([NH:8][C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])([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)O>C(N(CC)CC)C>[S:15]([O:11][CH2:10][C:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])([CH3:13])[CH3:12])(=[O:17])(=[O:16])[CH3:14]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 31297Methanesulfonyl chlorideHCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Product 1

HCID 11659022Methanesulfonic acid 2-tert-butoxycarbonylamino-2-methyl-propyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

N-Boc-2-Amino-2-methylpropanol is dissolved in triethylamine under argon at 0° C. Methanesulfonyl chloride is added and the mixture is stirred 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-2-amino-2-methyl-1-propyl 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-6e669e8cf7134e588878d14a9ac08ce2
Source dataset
uspto-grants-1987_10
Patent number
US04698231

Reaction notes

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