Ammonia → (S)-tert-butyl 1-amino-3-(4-nitrophenyl)-1-oxopropan-2-ylcarbamate

HRID 2193864Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:24]1CCOCC1.ClC(OCC(C)C)=O.N>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:10](=[O:11])[NH2:24])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 2-(S)-tert-butoxycarbonylamino-3-(4-nitrophenyl)-propionic acid and N-methylmorpholine (1.1 mL, 9.65 mmol) in DMF (10 mL) is added dropwise iso-butyl chloroformate (1.25 mL, 9.65 mmol). The mixture is stirred at 0° C. for 20 minutes. after which NH3 (g) is passed through the reaction mixture for 30 minutes at 0° C. The reaction mixture is concentrated and the residue dissolved in EtOAc, washed successively with 5% citric acid, water, 5% NaHCO3, water and brine, dried (Na2SO4), filtered and concentrated in vacuo to a residue that is triturated with a mixture of EtOAc/petroleum ether to provide 2.2 g (74% yield) of the desired product as a white solid.

Workup

concentrationThe reaction mixture is concentrated
dissolutionthe residue dissolved in EtOAc
washwashed successively with 5% citric acid, water, 5% NaHCO3, water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo to a residue that
customis triturated with a mixture of EtOAc/petroleum ether

Sources & evidence

ORD record: ord-54124443eadf48c692d563e02ceba26b
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329916B2

Reaction notes

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