Water → HCID 86704548, compound

HRID 633461Notes

Reaction equation

HRID 633461 reaction equation
[Si:1]([O:8][CH2:9][C:10]1([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[O:15][C:14]2[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:13]=2[N:12]2[C:23](=[O:26])[NH:24][N:25]=[C:11]12)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].IC.[C:38](=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Si:29]([O:28][CH2:27][C:10]1([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[O:15][C:14]2[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:13]=2[N:12]2[C:23](=[O:26])[N:24]([CH3:38])[N:25]=[C:11]12)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86704547HCID 86704547, compound

Product 1

HCID 86704548HCID 86704548, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,4-Bis(((tert-butyldimethylsilyl)oxy)methyl)-8-nitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one and iodomethane (0.626 mL) were dissolved in DMF. Cesium carbonate (4.13 g) was added to the solution. The reaction mixture was stirred at room temperature overnight. Water (250 mL) was added to the reaction. The aqueous solution was extracted with EtOAc (2×200 mL). The organic layers were evaporated to give 4,4-bis(((tert-butyldimethylsilyl)oxy)methyl)-2-methyl-8-nitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one.

Workup

  1. extractionThe aqueous solution was extracted with EtOAc (2×200 mL)
  2. customThe organic layers were evaporated

Sources & evidence

ORD record
ord-6282bd97eff14e8586b066607b50809f
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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