Hydrochloric Acid → HCID 90204562, compound

HRID 1480314Notes

Reaction equation

HRID 1480314 reaction equation
C(S([NH:7][CH:8]([C:13]1([CH3:17])[CH2:16][O:15][CH2:14]1)[C:9]([NH2:12])=[N:10][OH:11])=O)(C)(C)C.CO[C:20](OC)(N(C)C)[CH3:21].Cl.O1CCOCC1>C(O)(C)C.C(OCC)(=O)C>[CH3:20][C:21]1[O:11][N:10]=[C:9]([CH:8]([C:13]2([CH3:17])[CH2:14][O:15][CH2:16]2)[NH2:7])[N:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 131736607HCID 131736607, compound

Product 1

HCID 90204562HCID 90204562, compoundYield 20.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(tert-butylsulfinylamino)-N′-hydroxy-2-(3-methyloxetan-3-yl)acetamidine (example 254a, 0.25 g, 949 μmol) in isopropanol (5.00 ml) was added 1,1-dimethoxy-N,N-dimethylethanamine (506 mg, 3.8 mmol) and the reaction mixture was stirred at room temperature overnight. A solution of 4M hydrochloric acid in dioxane (1.19 ml, 4.75 mmol) was added to the reaction mixture cooled down to 0° C. and the reaction was stirred at 0° C. for 2 hours. The reaction mixture was diluted with ethyl acetate and extracted with a 2M aqueous solution of sodium carbonate. The organic phase was collected and the aqueous phase was back-extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a dichloromethane-methanol gradient to yield the title compound (35 mg, 20%) as a yellow oil which was not totally pure and was used without any further purification. MS (ESI, m/z): 184.1 (M+H+).

Workup

  1. temperaturecooled down to 0° C.
  2. stirringthe reaction was stirred at 0° C. for 2 hours
  3. extractionextracted with a 2M aqueous solution of sodium carbonate
  4. customThe organic phase was collected
  5. extractionthe aqueous phase was back-extracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. customevaporated down to dryness
  8. customThe crude material was purified by flash chromatography on silica eluting with a dichloromethane-methanol gradient

Sources & evidence

ORD record
ord-86a1b46840264472bf0b5803e2c41a88
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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