Triethyl(methoxycarbonylsulfamoyl)aminium → HCID 131728113, compound

HRID 1024108Notes

Reaction equation

HRID 1024108 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:17][CH2:16][C:15]([C:19]([CH3:27])([CH3:26])[O:20][SiH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])(O)[C@@H:14]2[C:28]2[CH:33]=[CH:32][C:31]([CH:34]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=3)[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:30][CH:29]=2)=[CH:8][CH:9]=1)=[O:4].C([N+](CC)(CC)S(NC(=O)OC)(=O)=O)C>C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:17][CH2:16][C:15]([C:19]([CH3:27])([CH3:26])[O:20][SiH2:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[C:14]2[C:28]2[CH:29]=[CH:30][C:31]([CH:34]([O:40][CH2:41][C:42]3[CH:43]=[CH:44][C:45]([O:48][CH3:49])=[CH:46][CH:47]=3)[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:32][CH:33]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 2724995Triethyl(methoxycarbonylsulfamoyl)aminiumHCID 131728114HCID 131728114, compound

Product 1

HCID 131728113HCID 131728113, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 21 (46 mg, 0.065 mmol) and methyl N-(triethylammoniumsulphonyl)carbamate (Burgess reagent, 62 mg, 0.26 mmol) in benzene (0.9 mL) was heated at 50° C. After 1 h, the reaction was quenched by addition of H2O and the resulting mixture was extracted with dichloromethane (3×20 mL). The combined organic solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (ethyl acetate/hexanes) gave the title compound (31 mg, 68%).

Workup

  1. customthe reaction was quenched by addition of H2O
  2. extractionthe resulting mixture was extracted with dichloromethane (3×20 mL)
  3. washThe combined organic solution was washed with brine
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash chromatography on silica gel (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d567d5ef5f8c4778bb458fe4bd199994
Source dataset
uspto-grants-2014_05
Patent number
US08722726B2

Reaction notes

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