Nitric Acid → HCID 46913784, compound

HRID 239012Notes

Reaction equation

[N+:1]([O-:4])(O)=[O:2].[C:5]([C:8]1[CH:29]=[CH:28][C:11]([O:12][CH2:13][C:14]2([NH:17][C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:16][CH2:15]2)=[C:10]([O:30][CH3:31])[CH:9]=1)(=[O:7])[CH3:6]>CC(OC(C)=O)=O>[C:5]([C:8]1[C:29]([N+:1]([O-:4])=[O:2])=[CH:28][C:11]([O:12][CH2:13][C:14]2([NH:17][C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:16][CH2:15]2)=[C:10]([O:30][CH3:31])[CH:9]=1)(=[O:7])[CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of HNO3 (65%, 3 mL) in Ac2O (2 mL) at 0° C. was slowly added with a suspension of the compound of Example 1 (1.1 g, 2.9 mmol) in Ac2O (3 mL) After stirring at 0° C. for 2 h, the reaction mixture was poured into 50 mL of ice/water and the precipitate was recovered by filtration. The resulting yellow solid was recrystallized with 95% EtOH (5 mL) to give 1-[(4-acetyl-2-methoxy-5-nitrophenoxy)methyl]-N-benzyloxycarbonyl-1-aminocyclopropane (0.69 g, yield: 56%) as a yellow solid.

Workup

filtrationthe precipitate was recovered by filtration
customThe resulting yellow solid was recrystallized with 95% EtOH (5 mL)

Sources & evidence

ORD record: ord-b31f1adeb26141bbb02a5740e2ed944d
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642767B2

Reaction notes

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