Hydroxylamine → HCID 86710151, compound

HRID 705342Notes

Reaction equation

HRID 705342 reaction equation
[C:1]([C:3]1[C:7]2[CH:8]=[C:9]([CH:26]3[CH2:28][CH2:27]3)[C:10]([N:12]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][C:6]=2[O:5][C:4]=1[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)#[N:2].[NH2:36][OH:37]>C(O)C>[CH:26]1([C:9]2[C:10]([N:12]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][C:6]3[O:5][C:4]([C:29]4[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=4)=[C:3]([C:1](=[N:36][OH:37])[NH2:2])[C:7]=3[CH:8]=2)[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86710152HCID 86710152, compound

Product 1

HCID 86710151HCID 86710151, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

To a 20 mL microwave tube was added the product from Example 8B (340 mg, 0.693 mmol) and hydroxylamine (50 weight % in water, 6.0 mL, 102 mmol) in ethanol (6 mL). The vial was sealed and heated in a microwave reactor (Personal Chemistry (Biotage), Emrys Creator, 300 W maximum) at 140° C. for 30 minutes. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to give the title compound which was used without purification (363 mg, quantitative yield). MS (ESI+) m/z 524 (M+H)+.

Workup

  1. customThe vial was sealed
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c2e8c3119501472c8f791e10df05e166
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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