Triethylamine → HCID 178466781, compound

HRID 1667604Notes

Reaction equation

HRID 1667604 reaction equation
Cl.[OH:2][NH2:3].C(N(CC)CC)C.[C:11]([C:13]1[CH:37]=[CH:36][C:16]([O:17][CH:18]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH:30]([CH3:32])[CH3:31])=[C:25]([O:33][CH2:34][CH3:35])[CH:24]=2)[C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=1)#[N:12]>CS(C)=O.C(OCC)(=O)C>[OH:2][NH:3][C:11]([C:13]1[CH:14]=[CH:15][C:16]([O:17][CH:18]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH:30]([CH3:32])[CH3:31])=[C:25]([O:33][CH2:34][CH3:35])[CH:24]=2)[C:19]([O:21][CH3:22])=[O:20])=[CH:36][CH:37]=1)=[NH:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 57448201HCID 57448201, compound

Product 1

HCID 178466781HCID 178466781, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To hydroxyamine HCl salt (363 mg, 5.2 mmol) in DMSO (5.0 mL) was added triethyl amine (0.725 mL, 5.2 mmol). After stirring at rt for 10 min, the cloudy solution was filtered directly into a round-bottom flask containing 9A (482 mg, 1.3 mmol). The mixture was stirred at 60° C. for 18 h before it was diluted with ethyl acetate and washed with 5% NaHCO3/brine. The organic extract was dried over Na2SO4 and concentrated to give 9B as a white solid. LC-MS 403 (M+H)+.

Workup

  1. filtrationthe cloudy solution was filtered directly into a round-bottom flask
  2. stirringThe mixture was stirred at 60° C. for 18 h before it
  3. washwashed with 5% NaHCO3/brine
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b1f2bf6a81244a688ec37f5d62602954
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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