Diisopropylethylamine → HCID 178431661, compound

HRID 72370Notes

Reaction equation

HRID 72370 reaction equation
C([NH:5][S:6]([CH2:9][CH:10]([NH2:18])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)(=[O:8])=[O:7])(C)(C)C.FC1C=CC=C(F)C=1O[C:23]1[O:24][C:25]([CH3:34])([CH3:33])[C:26]([CH3:32])([CH3:31])[S:27](=[O:30])(=[O:29])[N:28]=1.C(N(CC)C(C)C)(C)C>ClCCl.C(OCC)(=O)C>[F:17][C:14]1[CH:13]=[CH:12][C:11]([CH:10]([NH:18][C:23]2[O:24][C:25]([CH3:34])([CH3:33])[C:26]([CH3:32])([CH3:31])[S:27](=[O:30])(=[O:29])[N:28]=2)[CH2:9][S:6]([NH2:5])(=[O:7])=[O:8])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 68287917N-(tert-Butyl)-2-amino-2-(4-fluorophenyl)ethanesulfonamideHCID 867054542-(2,6-Difluorophenoxy)-5,5,6,6-tetramethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Product 1

HCID 178431661HCID 178431661, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

50 mg of N-(tert-Butyl)-2-amino-2-(4-fluorophenyl)ethanesulfonamide enantiomer 1 and 58 mg of 2-(2,6-difluorophenoxy)-5,5,6,6-tetramethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide were dissolved in 1 ml of dichloromethane, and the mixture was stirred at room temperature for 5 hours. The completeness of the conversion was checked by LCMS. Since no conversion had taken place yet, 60 μl of N,N-diisopropylethylamine were added and the mixture was stirred at room temperature overnight. The reaction solution was diluted with 20 ml of ethyl acetate and washed with 10 ml of 0.1 N hydrochloric acid and 10 ml of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated by rotary evaporation. The residue was dissolved in 1 ml of trifluoroacetic acid and dissolved at room temperature for 20 hours. After the removal of the solvent under reduced pressure, the crude product was purified in a purification laboratory by means of preparative HPLC. After lyophilization of the product-containing fractions, the product (25.8 mg) was obtained with a molecular weight of 407.5 g/mol (C15H22FN3O5S2); MS (ESI): m/e=408 (M+H+).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. washwashed with 10 ml of 0.1 N hydrochloric acid and 10 ml of saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. dissolutionThe residue was dissolved in 1 ml of trifluoroacetic acid
  6. dissolutiondissolved at room temperature for 20 hours
  7. customAfter the removal of the solvent under reduced pressure
  8. customthe crude product was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-be49cd2e9f5a4100a54031cdfc86a6b5
Source dataset
uspto-grants-2014_09
Patent number
US08828994B2

Reaction notes

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