Hydroxylamine → HCID 178455217, compound
Reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:18]1[C:35]([CH:36]2[CH2:38][CH2:37]2)=[CH:34][C:21]2[C:22]([C:32]#[N:33])=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[O:24][C:20]=2[CH:19]=1)[S:14]([CH3:17])(=[O:16])=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:39][OH:40]>C(O)C>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([S:14]([CH3:17])(=[O:16])=[O:15])[C:18]1[C:35]([CH:36]2[CH2:38][CH2:37]2)=[CH:34][C:21]2[C:22]([C:32](=[NH:33])[NH:39][OH:40])=[C:23]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[O:24][C:20]=2[CH:19]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]Participants
4
Conditions
- Temperature
- 140 °C
Procedure
To a 20-mL microwave tube was added a solution of Example 11B (0.1346 g, 0.242 mmol) in ethanol (3 mL) followed by hydroxylamine (50 weight % in water, 3 mL, 50.9 mmol). The tube was sealed and the thick slurry was heated in a microwave reactor (Personal Chemistry (Biotage), Emrys Creator, 300 W maximum) for 30 minutes at 140° C. The reaction mixture was concentrated in vacuo to a cloudy solution that was taken up in ethyl acetate (60 mL), washed with 10% aqueous NaCl, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford the title compound as a foamy white solid (0.119 g, 84%).
Workup
- customThe tube was sealed
- concentrationThe reaction mixture was concentrated in vacuo to a cloudy solution that
- washwashed with 10% aqueous NaCl
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1518a5620e35426ba4488c093397918c
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09173887B2
Reaction notes
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