N-Methyl-N-nitrosourea → HCID 86656344, compound

HRID 1942461Notes

Reaction equation

HRID 1942461 reaction equation
N(N(C)[C:4](N)=O)=O.[OH-].[K+].[CH2:10]([N:16]1[C:21]2[CH:22]=[C:23]([C:27]([N:29]([CH:43]([CH3:45])[CH3:44])[C@@H:30]3[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31]3)=[O:28])[C:24]([CH3:26])=[CH:25][C:20]=2[O:19][C:18]([CH3:47])([CH3:46])[C:17]1=[O:48])[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15].C(Cl)(Cl)Cl.C(OCC)C>C(OCC)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:14]1([CH2:13][CH2:12][CH2:11][CH2:10][N:16]2[C:21]3[CH:22]=[C:23]([C:27]([N:29]([CH:43]([CH3:44])[CH3:45])[C@@H:30]4[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:31]4)=[O:28])[C:24]([CH3:26])=[CH:25][C:20]=3[O:19][C:18]([CH3:46])([CH3:47])[C:17]2=[O:48])[CH2:4][CH2:15]1

Participants

8

Reactant 4

HCID 12699N-Methyl-N-nitrosoureaHCID 14797Potassium HydroxideHCID 21911965Chloroform etherHCID 67332410HCID 67332410, compound

Product 1

HCID 86656344HCID 86656344, compoundYield 81.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

N-Nitroso-N-methylurea (2.62 g) was dissolved in diethyl ether (34 ml), and the mixture was added dropwise into a solution of potassium hydroxide (1.53 g) in water (9 ml) under ice-cooling, and the mixture was stirred at 0° C. for 15 minutes. Then, the obtained supernatant was added dropwise to a solution of tert-butyl (3R)-3-[[(4-hex-5-en-1-yl-2,2,7-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl](isopropyl)amino]piperidine-1-carboxylate (300 mg) with palladium acetate (15 mg) in a mixed solvent of chloroform/diethyl ether. The mixture was stirred at room temperature for one hour. After the reaction was complete, the mixture was filtered and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give the title compound (250 mg) as a colorless liquid.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for one hour
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-ad369a3ed3614681a7f10d583ebf5af9
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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