Triethylamine → HCID 178460881, compound

HRID 1480171Notes

Reaction equation

HRID 1480171 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[NH:10][C:11]([C:18]#[N:19])([CH3:17])[CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[NH2:29][OH:30]>C(O)C>[CH2:1]([O:8][C:9](=[O:20])[NH:10][C:11]([C:18](=[NH:19])[NH:29][OH:30])([CH3:17])[CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 90204048(1-Cyano-2-methanesulfonyl-1-methyl-ethyl)-carbamic acid benzyl ester

Product 1

HCID 178460881HCID 178460881, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (1-Cyano-2-methanesulfonyl-1-methyl-ethyl)-carbamic acid benzyl ester (Example 109a, 3.07 g, 10.4 mmol) in dry ethanol (58 ml) were added triethylamine (2.17 mL, 15.5 mmol) and hydroxylamine hydrochloride (936 mg, 13.5 mmol). The reaction mixture was then stirred at 60° C. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethylacetate and extracted with an 1.0M aqueous solution of sodium carbonate. The organic phase was collected and the aqueous phase was back-extracted with ethylacetate. 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 ethyl acetate/heptane gradient to yield the title compound (2.04 gr, 60%) as a white powder. MS (ESI, m/z): 330.6 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethylacetate
  3. extractionextracted with an 1.0M aqueous solution of sodium carbonate
  4. customThe organic phase was collected
  5. extractionthe aqueous phase was back-extracted with ethylacetate
  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 ethyl acetate/heptane gradient

Sources & evidence

ORD record
ord-ba34cb3e9d85426a97c1d5571d45f7d1
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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