Hydroxylamine → HCID 10317331, compound

HRID 1723908Notes

Reaction equation

HRID 1723908 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([O:15][C:16]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:17]=2[C:18](O)=[O:19])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].O.[OH:27][N:28]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.NO>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([O:15][C:16]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:17]=2[C:18]([NH:28][OH:27])=[O:19])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18448188HCID 18448188, compound

Product 1

HCID 10317331HCID 10317331, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.125 g (0.347 mmol) of the product of Step 2 in 4.4 mL of N,N-dimethylformamide (DMF) is added 0.056 g (0.417 mmol) of 1-hydroxybenzotriazole hydrate (HOBT) followed by 0.089 g (0.462 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC). The resulting mixture is stirred for 1 h at room temperature and then 0.095 mL of a 50% aqueous solution of hydroxylamine is added and the reaction mixture is stirred overnight. The reaction mixture is then diluted with ethyl acetate and washed with water and brine. The organics are dried over sodium sulfate, filtered and concentrated in vacuo. The residue is chromatographed on silica gel eluting with a gradient of ethyl acetate-hexanes (1:1 to 2:1) to provide 0.065 g (50%) of 2-[(hydroxyamino)carbonyl]-6-methylphenyl 4-(2-butynyloxy)benzenesulfonate as a white solid. Electrospray Mass Spec: 376.0 (M+H)+

Workup

  1. stirringthe reaction mixture is stirred overnight
  2. washwashed with water and brine
  3. dry with materialThe organics are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on silica gel eluting with a gradient of ethyl acetate-hexanes (1:1 to 2:1)

Sources & evidence

ORD record
ord-0e5a9bbf5ccf4fec86e7b4f884bbf2f3
Source dataset
uspto-grants-2009_02
Patent number
US07485667B2

Reaction notes

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