tert-Butyldimethylsilyl chloride → HCID 86704520, compound

HRID 633424Notes

Reaction equation

HRID 633424 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si:9]([O:16][CH2:17][C:18]1([CH2:32][OH:33])[O:23][C:22]2[CH:24]=[CH:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:21]=2[NH:20][C:19]1=[O:31])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>>[Si:1]([O:33][CH2:32][C:18]1([CH2:17][O:16][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:11])[O:23][C:22]2[CH:24]=[CH:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:21]=2[NH:20][C:19]1=[O:31])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 131735470HCID 131735470, compound

Product 1

HCID 86704520HCID 86704520, compound

Procedure

Another experiment using 3 equiv. of TBS-Cl with 1.02 g of 2,2-bis(hydroxymethyl)-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one, gave the pure product (0.62 g, 32% yield), followed by the product with TBS-Cl (0.8 g), followed by mono-silylated material-2-(((tert-butyldimethylsilyl)oxy)methyl)-2-(hydroxymethyl)-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (0.56 g, 38%)

Sources & evidence

ORD record
ord-483a27dda29942b89886f55e23664cae
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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