6-amino-3,4-dihydro-2H-1,4-benzothiazin-3-one → Rac-6-[6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-hexylamino]-4h-benzo[1,4]thiazin-3-one

HRID 527972Notes

Reaction equation

HRID 527972 reaction equation
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:13][O:12]1)([CH3:4])([CH3:3])[CH3:2].[NH2:16][C:17]1[CH:18]=[CH:19][C:20]2[S:25][CH2:24][C:23](=[O:26])[NH:22][C:21]=2[CH:27]=1>CCO.O>[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:12])[CH2:13][NH:16][C:17]1[CH:18]=[CH:19][C:20]2[S:25][CH2:24][C:23](=[O:26])[NH:22][C:21]=2[CH:27]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6869016-amino-3,4-dihydro-2H-1,4-benzothiazin-3-oneHCID 13570755Rac-tert-butyl-dimethyl-(4-oxiranyl-butoxy)-silane

Product 1

HCID 67349822Rac-6-[6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-hexylamino]-4h-benzo[1,4]thiazin-3-oneYield 42%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of 2-[4-[(tert-butyl)dimethylsiloxy]butyl]oxirane (10.0 g) and 6-amino-4H-benzo[1,4]thiazin-3-one (7.81 g; commercial) in EtOH/water (300 mL; 9:1) was refluxed for 2 days. The solvents were removed under reduced pressure and the residue was taken up in EA/Hex (1:1; 100 mL) and filtered. The filtrate was concentrated under reduced pressure and purified by CC (EA/Hex; 1:1), affording an orange solid (7.40 g; 42% yield).

Workup

  1. customThe solvents were removed under reduced pressure
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. custompurified by CC (EA/Hex; 1:1)
  5. customaffording an orange solid (7.40 g; 42% yield)

Sources & evidence

ORD record
ord-15f2fe81e2114e3abfff2451532968f4
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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