Methyl chloroformate → N-tert.-butyl-2-dimethylaminocarbonyl-5-methoxycarbonylamino-benzenesulfonamide

HRID 2300974Notes

Reaction equation

HRID 2300974 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])=[C:11]([S:13]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])=[O:14])[CH:12]=1.C([O-])(O)=O.[Na+]>CC#N.C(OCC)(=O)C>[C:17]([NH:16][S:13]([C:11]1[CH:12]=[C:7]([NH:6][C:2]([O:4][CH3:5])=[O:3])[CH:8]=[CH:9][C:10]=1[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])(=[O:15])=[O:14])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 152405445-Amino-n-tert.-butyl-2-dimethylaminocarbonylbenzenesulfonamide

Product 1

HCID 15240545N-tert.-butyl-2-dimethylaminocarbonyl-5-methoxycarbonylamino-benzenesulfonamideYield 83.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.47 g of methyl chloroformate is added dropwise to a suspension of 1.50 g of 5-amino-N-tert.-butyl-2-dimethylaminocarbonyl-benzenesulfonamide (Example e) and 1.46 g of NaHCO3 in 50 ml of CH3CN at 0° C. When the reaction has ended, the reaction mixture is taken up in ethyl acetate and the mixture is washed with 1N hydrochloric acid, dried over MgSO4 and concentrated. 1.48 g of N-tert.-butyl-2-dimethylaminocarbonyl-5-methoxycarbonylamino-benzenesulfonamide are thus obtained; m.p.: 184-188° C.

Workup

  1. washthe mixture is washed with 1N hydrochloric acid
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cde37942d3594074b26781c671cffbf3
Source dataset
uspto-grants-2002_12
Patent number
US06498253B1

Reaction notes

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