Tetrahydrofuran → HCID 11150428, compound

HRID 1059313Notes

Reaction equation

HRID 1059313 reaction equation
[Si](OCC[C:11]1[CH:27]=[N:26][C:14]2[S:15][C:16]3[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=3[N:18]([CH2:19][O:20][CH3:21])[C:13]=2[N:12]=1)(C(C)(C)C)(C)C.[O:28]1CC[CH2:30][CH2:29]1>>[CH3:21][O:20][CH2:19][N:18]1[C:17]2[CH:22]=[C:23]([CH2:30][CH2:29][OH:28])[CH:24]=[CH:25][C:16]=2[S:15][C:14]2[N:26]=[CH:27][CH:11]=[N:12][C:13]1=2

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 86592276HCID 86592276, compound

Product 1

HCID 11150428HCID 11150428, compound

Procedure

463 mg of 8-[(2-(tert-butyldimethylsilyloxy)ethyl]-10-(methoxymethyl)-10H-pyrazino[2,3-b][1,4]benzothiazine was dissolved in 5 ml of tetrahydrofuran. After adding 1.3 ml of n-tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran), the resulting mixture was stirred at room temperature for 1 hour and then at 4° C. for additional 13 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 281 mg of the title compound as a pale orange solid.

Workup

  1. waitat 4° C. for additional 13 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5dee27b1c1814a85b02ce142f9ab1a47
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

Loading…