Nitrogen → HCID 131730012, compound

HRID 42866Notes

Reaction equation

HRID 42866 reaction equation
N#N.C([O:5][C:6]([C:8]1[N:9]=[C:10]([C:13]([CH3:21])([CH3:20])[O:14][SiH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[O:11][CH:12]=1)=O)C.CC(C[AlH]CC(C)C)C>C1COCC1.C1(C)C=CC=CC=1.CC(=O)OCC.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>[C:16]([SiH2:15][O:14][C:13]([CH3:21])([CH3:20])[C:10]1[O:11][CH:12]=[C:8]([CH2:6][OH:5])[N:9]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

8

Reactant 3

HCID 947NitrogenHCID 14487Diisobutylaluminum hydrideHCID 131730007HCID 131730007, compound

Product 1

HCID 131730012HCID 131730012, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 9357Potassium Sodium TartrateSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazole-4-carboxylic acid ethyl ester (830 mg, 2.91 mmol) in THF (15.0 mL) was treated at 0° C. with DiBAL (11.6 mL of a 1M sol in toluene, 11.60 mmol) and the reaction mixture was stirred for 45 min at 0° C. The reaction mixture was then diluted with EA (5.0 mL), sat. aq. Rochelle's salt (20.0 mL) was added and the mixture stirred at rt for 2 h. The layers were separated and the aq. layer extracted with EA (3×20 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow solid. TLC: rf (EA)=0.59. LC-MS-conditions 02: tR=0.94 min; [M+H]+=244.46.

Workup

  1. additionwas added
  2. stirringthe mixture stirred at rt for 2 h
  3. customThe layers were separated
  4. extractionthe aq. layer extracted with EA (3×20 mL)
  5. dry with materialextracts were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-03425e29addd4b0da28afeb898b6dc6b
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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