Sodium hydride → HCID 68574727, compound

HRID 1714812Notes

Reaction equation

HRID 1714812 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH:18]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH2:17][N:16]([C:30]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[CH2:15][CH:14]2[OH:40])=[CH:9][CH:8]=1)[CH:4]=[CH2:5].Cl[CH2:42][C:43]1[CH:44]=[CH:45][C:46]2[O:51][CH2:50][C:49](=[O:52])[N:48]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[C:47]=2[CH:58]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH:18]([O:19][Si:20]([CH:24]([CH3:26])[CH3:25])([CH:27]([CH3:29])[CH3:28])[CH:21]([CH3:22])[CH3:23])[CH2:17][N:16]([C:30]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[CH2:15][CH:14]2[O:40][CH2:42][C:43]2[CH:44]=[CH:45][C:46]3[O:51][CH2:50][C:49](=[O:52])[N:48]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[C:47]=3[CH:58]=2)=[CH:9][CH:8]=1)[CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 468352236-(chloromethyl)-4-(3-methoxypropyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneHCID 68574797HCID 68574797, compound

Product 1

HCID 68574727HCID 68574727, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

1.61 g of sodium hydride dispersion (60%) are added to a solution of 19.76 g of benzyl 4-(4-allyloxyphenyl)-3-hydroxy-5 -triisopropylsilanyloxypiperidine-1-carboxylate and 9.95 g of 6-chloromethyl-4-(3-methoxypropyl)-4H-benz[1,4]-oxazin-3-one in 285 ml of N,N-dimethylformamide while the reaction mixture is stirred at 10° C. for 1 hour and at room temperature for 18 hours. The mixture is poured into 1M aqueous sodium bicarbonate solution (700 ml) and extracted with tert-butyl methyl ether 2×800 ml). The organic phases are washed successively with water (2×500 ml) and brine (1×500 ml), dried with sodium sulphate and evaporated. The title compound is obtained from the residue by flash chromatography (SiO260 F). Rf (EtOAc/heptane 2:3)=0.30, Rt=7.15.

Workup

  1. extractionextracted with tert-butyl methyl ether 2×800 ml)
  2. washThe organic phases are washed successively with water (2×500 ml) and brine (1×500 ml)
  3. dry with materialdried with sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-1ea9f595c28a42fcb3bd34d3df8f2303
Source dataset
uspto-grants-2010_09
Patent number
US07799779B2

Reaction notes

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