HOAt → HCID 22346258, compound

HRID 897340Notes

Reaction equation

HRID 897340 reaction equation
OC(C(F)(F)F)=O.[S:8](=[N:11][CH2:12][C:13]([OH:15])=O)(=[O:10])=[O:9].ON1[C:21]2[N:22]=[CH:23][CH:24]=C[C:20]=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(N(C(C)C)CC)(C)C>[CH2:21]([N:22]1[CH2:23][CH2:24][S:8](=[O:10])(=[O:9])[NH:11][CH2:12][C:13]1=[O:15])[CH3:20]

Participants

6

Reactant 3

HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86587465HCID 86587465, compound

Product 1

HCID 22346258HCID 22346258, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a mixture of the above N-sulfonylglycine TFA salt (0.32 g, 0.98 mmol), 1-hydroxy-7-azabenzotriazole (36 mg, 0.26 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.22 g, 1.13 mmol) in DMF (50 mL), diisopropyl-ethylamine was added dropwise to adjust the pH to 5-6, and the resultant mixture was stirred at room temp overnight. The reaction mixture was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluted with chloroform. Collection and concentration of appropriate fractions provided 5-ethyl-1,2,5-thiadiazepan-4-one 1,1-dioxide as white solid.

Workup

  1. additionwas added dropwise
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. washeluted with chloroform
  4. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-e4179ec79a5b4318b74d7261ebd28453
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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