Acetyl chloride → [(Z)-[(2S)-1-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]propylidene]amino] acetate
Reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@@H:8]([CH3:13])/[C:9](/[NH2:12])=[N:10]/[OH:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>C(Cl)Cl>[C:22]([O:11]/[N:10]=[C:9](\[NH2:12])/[C@@H:8]([NH:7][C:6](=[O:14])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH3:13])(=[O:24])[CH3:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of tert-butyl[(1S,2Z)-2-amino-2-(hydroxyimino)-1-methylethyl]carbamate (Step 3, 100 mg, 0.5 mmol) in methylene chloride (2 mL) cooled at 0° C. was added triethylamine (0.10 mL, 0.74 mmol). To the mixture was then added acetyl chloride (42 mg, 0.54 mmol) dropwise and the reaction was warmed to room temperature. After stirring at room temperature for 1 h, the reaction was concentrated. The residue was dissolved in dichloromethane (DCM), washed with water and brine, dried over MgSO4, filtered and concentrated to afford the desired crude product (100 mg, 82.8%) which was directly used in the next step reaction without further purification. 1H-NMR (300 MHz, DMSO-d6): 6.90 (d, J=9.0 Hz, 1H), 6.22 (s, 2H), 4.05 (m, 1H), 2.01 (s, 3H), 1.36 (s, 9H), 1.20 (d, J=7.0 Hz, 3H).
Workup
- concentrationthe reaction was concentrated
- dissolutionThe residue was dissolved in dichloromethane (DCM)
- washwashed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e64e2529e4fc49cda7a16e38dbca3238
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08487096B2
Reaction notes
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