N-Boc-p-toluenesulfonamide → tert-Butyl methyl(tosyl)carbamate

HRID 393410

Reaction equation

HRID 393410 reaction equation
[CH3:1]COC(/N=N/C(OCC)=O)=O.[C:13]([NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CO>[CH3:1][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 688170N-Boc-p-toluenesulfonamideHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22660067tert-Butyl methyl(tosyl)carbamateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude fluorous DEAD reagent 22 was then used in Mitsunobu reactions with N-Boc-p-toluenesulfonamide. Once again, the standard mode of addition gave complete conversion with MeOH and the product, N-methyl-N-boc-p-toluenesulfonamide was isolated in 85% yield after FSPE. However, the allyl alcohol gave only trace conversion of the starting material. The organic fraction after FSPE was mostly starting material. These results are summarized in Table 7.

Workup

  1. additionOnce again, the standard mode of addition

Sources & evidence

ORD record
ord-41a99d97be5e482e8c5bb07a1cfdf604
Source dataset
uspto-grants-2004_10
Patent number
US06806357B1

Linked notes

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