Methyl N-(triethylammoniosulfonyl)carbamate → HCID 118308725, compound

HRID 923487Notes

Reaction equation

HRID 923487 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1([CH3:22])[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[N:9]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O)(=[O:3])[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClC(Cl)C>[CH3:13][C:10]1([CH3:14])[N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[C:8]([CH3:22])([C:6]2[O:3][C:1]([CH3:2])=[N:4][N:5]=2)[CH2:12][O:11]1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 118308731HCID 118308731, compound

Product 1

HCID 118308725HCID 118308725, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 320 mg of tert-butyl 4-[(2-acetylhydrazino)carbonyl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate in 10 ml of dichloroethane was added 358 mg of a Burgess reagent ((methoxycarbonylsulfamoyl)triethylammonium hydroxide inner salt), followed by stirring at 80° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 84 mg of tert-butyl 2,2,4-trimethyl-4-(5-methyl-1,3,4-oxadiazol-2-yl)-1,3-oxazolidine-3-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e64afa4fd74047acbde12e0c67d9593d
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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