HCID 18521101, compound → HCID 135991626, compound

HRID 369546Notes

Reaction equation

HRID 369546 reaction equation
C(OC1C(N)=CC(O)=C([N+]([O-])=O)C=1)CCCCCC.N([O-])=O.[Na+].Cl.C(O)C.C[C@H:29]([O:36][C:37]1[C:42]([N:43]=[N:44][C:45]2[CH:50]=[C:49]([O:51][C@@H:52]([CH3:59])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C:48]([N:60]([CH3:62])[CH3:61])=[CH:47][C:46]=2[OH:63])=[CH:41][C:40]([OH:64])=[C:39]([N+:65]([O-:67])=[O:66])[CH:38]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>N1C=CC=CC=1>[CH2:29]([O:36][C:37]1[C:42]([N:43]=[N:44][C:45]2[CH:50]=[C:49]([O:51][C@@H:52]([CH3:59])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C:48]([N:60]([CH3:61])[CH3:62])=[CH:47][C:46]=2[OH:63])=[CH:41][C:40]([OH:64])=[C:39]([N+:65]([O-:67])=[O:66])[CH:38]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 4

HCID 18521101HCID 18521101, compoundHCID 21887872Ethanol hydrochlorideHCID 23668193Sodium NitriteHCID 135971980HCID 135971980, compound

Product 1

HCID 135991626HCID 135991626, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 43a (388 mg, 1.46 mmol), compound 51b (392 mg, 1.46 mmol), 0.1M aqueous sodium nitrite (14.5 ml), and pyridine (4.5 ml) in 39 ml of a 15% HCl/ethanol solution were reacted according to the procedure for compound 52a. The crude product was adsorbed onto silica gel and purified via flash chromatography with gradual elutions from 90/5/5 to 75/20/5 (Hex/EtOAc/dichloromethane). Recrystallization from hexanes yielded 370 mg (46%) of a metallic green solid.

Workup

  1. custompurified via flash chromatography with gradual elutions from 90/5/5 to 75/20/5 (Hex/EtOAc/dichloromethane)
  2. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-fd5dc6f3d0c94e12b67e6e1fd29d3e9f
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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