Acetic Acid → HCID 66649411, compound
Reaction equation
[C:1]([O:9][C@@H:10]1[C@H:14]([O:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([CH2:24][O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:12][C@H:11]1[N:34]1[C:41](=[O:42])[CH:40]=[C:38]([NH2:39])[NH:37][C:35]1=[O:36])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:43]([O-])=O.[Na+].C(O)(=O)C>C(O)(C)=O.O.[Zn]>[NH2:43][C:40]1[C:41](=[O:42])[N:34]([C@@H:11]2[O:12][C@H:13]([CH2:24][O:25][C:26](=[O:33])[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C@@H:14]([O:15][C:16](=[O:23])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@H:10]2[O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:35](=[O:36])[NH:37][C:38]=1[NH2:39]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -5 °C
Procedure
To a solution of 49 (238 mg, 0.42 mmol) in AcOH—H2O (5: 0.5 mL) was added NaNO2 over 10 min at −5° C. The resulting mixture was stirred at −5° C. for 1 hr, concentrated, and co-evaporated with toluene to give a purple solid, which was treated with acetic acid (5 mL) and Zn dust (460 mg, 7.04 mmol), and heated at 70° C. for 30 mm. The mixture was filtered through a Celite pad, and the filtrate concentrated to a slightly green solid, which was purified by silica gel column chromatography (CHCl3:MeOH=10:1 v/v) to give compound 50 (217 mg, 88%).
Workup
- concentrationconcentrated
- customco-evaporated with toluene to give a purple solid, which
- temperatureheated at 70° C. for 30 mm
- filtrationThe mixture was filtered through a Celite pad
- concentrationthe filtrate concentrated to a slightly green solid, which
- customwas purified by silica gel column chromatography (CHCl3:MeOH=10:1 v/v)
Sources & evidence
- ORD record
- ord-918df35949cd4405a0f5086e280172dd
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093380B2
Reaction notes
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