Nitric Acid → 5-[2,4-bis(benzyloxy)-5-chlorophenyl]-N-ethyl-4-nitroisoxazole-3-carboxamide

HRID 389928Notes

Reaction equation

[CH2:1]([NH:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][C:12]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:8][N:7]=1)=[O:5])[CH3:2].[N+:34]([O-])([OH:36])=[O:35]>CC(OC(C)=O)=O>[CH2:27]([O:26][C:12]1[CH:13]=[C:14]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([Cl:17])=[CH:16][C:11]=1[C:9]1[O:8][N:7]=[C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])[C:10]=1[N+:34]([O-:36])=[O:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 5-(2,4-bis-benzyloxy-5-chloro-phenyl)-isoxazole-3-carboxylic acid ethylamide (1 g, 2.2 mmol) in Ac2O (20 ml) was cooled to 0° C. and HNO3 (0.26 ml, 4.3 mmol) was added dropwise under stirring, the temperature being maintained between 0-5° C. After the addition was complete, the mixture was stirred for 70 h at 5-10° C. and then poured into ice and extracted with DCM (3×40 ml). The extract was dried and concentrated under vacuo. The yellow solid obtained was triturated with Et2O and filtered to give 5-[2,4-bis(benzyloxy)-5-chlorophenyl]-N-ethyl-4-nitroisoxazole-3-carboxamide (810 mg, 73%).

Workup

temperaturethe temperature being maintained between 0-5° C
additionAfter the addition
stirringthe mixture was stirred for 70 h at 5-10° C.
additionpoured into ice
extractionextracted with DCM (3×40 ml)
customThe extract was dried
concentrationconcentrated under vacuo
customThe yellow solid obtained
customwas triturated with Et2O
filtrationfiltered

Sources & evidence

ORD record: ord-a17c52d484814569beadb63649b79146
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383616B2

Reaction notes

Loading…