Hydroxylamine → tert-butyl N-[(1Z,2S)-1-amino-1-hydroxyiminopropan-2-yl]carbamate
Reaction equation
[C:1]([C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4])#[N:2].C(N(CC)CC)C.[NH2:20][OH:21]>C(O)C>[NH2:2]/[C:1](=[N:20]\[OH:21])/[C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4]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-5a9bfd6dbb7b4aa89779ed5fccec2b38
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221824B2
Reaction notes
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