Hydroxylamine → tert-butyl N-[(1Z,2S)-1-amino-1-hydroxyiminopropan-2-yl]carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][C@H:8]([C:10]#[N:11])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[NH2:20][OH:21]>C(O)C>[C:1]([O:5][C:6](=[O:12])[NH:7][C@@H:8]([CH3:9])/[C:10](/[NH2:11])=[N:20]/[OH:21])([CH3:4])([CH3:2])[CH3:3]Participants
5
Conditions
- Temperature
- 50 °C
Procedure
To a mixture of tert-butyl[(1S)-1-cyanoethyl]carbamate (Step 2, 250 mg, 1.5 mmol) in ethanol (3 mL) were added triethylamine (0.41 mL, 2.9 mmol) and hydroxylamine (58 mg, 1.8 mmol). The mixture was stirred at 50° C. overnight. The reaction mixture was concentrated to afford the desired crude product (300 mg) which was directly used in the next step reaction without further purification. 1H-NMR (300 MHz, DMSO-d6): 8.94 (s, 1H), 6.80 (d, J=8.5 Hz, 1H), 5.24 (s, 2H), 4.01 (m, 1H), 1.36 (s, 9H), 1.15 (d, J=7.0 Hz, 3H).
Workup
- concentrationThe reaction mixture was concentrated
Sources & evidence
- ORD record
- ord-b18d9f1e00b74860a5fd05bb076174c7
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08487096B2
Reaction notes
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