tert-Butyldimethylsilyl chloride → HCID 54208717, compound

HRID 226205Notes

Reaction equation

HRID 226205 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]=2[O:5]1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C)C=O.C(N(CC)C(C)C)C>[O:1]([CH2:2][CH2:3][CH:4]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]=2[O:5]1)[Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 37401382-(2-Hydroxyethyl)-6-nitro-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 54208717HCID 54208717, compoundYield 14.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 521913N,N-Diethyl-2-propanamineSolvent

Conditions

Temperature
0 °C

Procedure

To solution of 4.8 g racemic-2-(2-hydroxyethyl)-6-nitro-3-oxo-4H-benz[1,4]oxazine in dimethylformamide (100 mL) and 3.4 mL diethylisopropylamine at 0° C. was added 4.7 g tert-butyldimethylsilylchloride. The reaction mixture was stirred at 0° C. for 20 minutes, at room temperature for 3 hour, concentrated and the resulting residue was partitioned between sodium bicarbonate solution and EtOAc. The aqueous phase was extracted with EtOAc and the combined organics washed with water, brine then dried over MgSO4. The solvent was removed by in vacuo and the crude material purified by column chromatography (hexanes/EtOAc) to yield 1 g of the desired product racemic-2-(2-t-butyldimethylsiloxyethyl)-6-nitro-3-oxo-4H-benz[1,4]oxazine MS (m/e): 353 (MH+).

Workup

  1. concentrationconcentrated
  2. customthe resulting residue was partitioned between sodium bicarbonate solution and EtOAc
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washthe combined organics washed with water, brine
  5. dry with materialthen dried over MgSO4
  6. customThe solvent was removed by in vacuo
  7. customthe crude material purified by column chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-fd3d709aecdc40f99a1ec7958cd30c28
Source dataset
uspto-grants-2009_07
Patent number
US07557207B2

Reaction notes

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