Diethyl Ether → N-t-butoxycarbonyl-N-methyl mesitylenesulfonylhydroxylamine

HRID 372458

Reaction equation

HRID 372458 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:10])[OH:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:11]1([CH3:23])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[S:19](Cl)(=[O:21])=[O:20].CCOCC>C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]([CH3:10])[O:9][S:19]([C:12]1[C:13]([CH3:18])=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=1[CH3:23])(=[O:21])=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 130462-Mesitylenesulfonyl chlorideHCID 272414tert-Butyl hydroxy(methyl)carbamate

Product 1

HCID 12948661N-t-butoxycarbonyl-N-methyl mesitylenesulfonylhydroxylamine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 16 g. of N-t-butoxycarbonyl-N-methyl hydroxylamine and 23.8 g. of mesitylenesulfonyl chloride in 400 ml. of ether was cooled to 0° C. and treated with 15.4 ml. of triethylamine dropwise with stirring. Thirty minutes after the addition was complete, the mixture was filtered, and the filter cake was washed with 2 portions of ether. The filtrate and washings were evaporated to a heavy oil. The oil was dissolved in 40 ml. of benzene, filtered through diatomaceous earth and concentrated to dryness to give a crystalline residue of N-t-butoxycarbonyl-N-methyl mesitylenesulfonylhydroxylamine, which was used directly in the next step without characterization.

Workup

  1. additiontreated with 15.4 ml
  2. additionThirty minutes after the addition
  3. filtrationthe mixture was filtered
  4. washthe filter cake was washed with 2 portions of ether
  5. customThe filtrate and washings were evaporated to a heavy oil
  6. dissolutionThe oil was dissolved in 40 ml
  7. filtrationof benzene, filtered through diatomaceous earth
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c4d0967b81d645c0a3a09114d2c46f88
Source dataset
uspto-grants-1978_05
Patent number
US04091105

Linked notes

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