Sodium Chloride → HCID 178440790, compound

HRID 1078208Notes

Reaction equation

[C:1]([C:5]1[C:6]([OH:40])=[C:7]([C:29]([CH3:39])([CH3:38])[CH2:30][O:31]C2CCCCO2)[CH:8]=[C:9]([CH:28]=1)[CH:10]=[C:11]1[C:16](=[O:17])[N:15]([CH2:18][C:19]2[NH:23][N:22]=[N:21][N:20]=2)[C:14]2[CH:24]=[CH:25][CH:26]=[CH:27][C:13]=2[S:12]1)([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl-].[Na+]>CO.C(Cl)(Cl)Cl>[C:1]([C:5]1[C:6]([OH:40])=[C:7]([C:29]([CH3:39])([CH3:38])[CH2:30][OH:31])[CH:8]=[C:9]([CH:28]=1)[CH:10]=[C:11]1[C:16](=[O:17])[N:15]([CH2:18][C:19]2[NH:23][N:22]=[N:21][N:20]=2)[C:14]2[CH:24]=[CH:25][CH:26]=[CH:27][C:13]=2[S:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

2-[5-tert.-Butyl-4-hydroxy-3-[1,1-dimethyl-2-(tetrahydropyran-2-yloxy)ethyl]benzylidene]-3,4-dihydro-3-oxo-4-(1H-tetrazol-5-ylmethyl)-2H-1,4-benzothiazine (compound No. 2-2, 0.31 g) was dissolved in a mixture of methanol (5 ml) and chloroform (1 ml). To the mixture, p-toluenesulfonic acid monohydrate (0.05 g) was added and the mixture was stirred for 3 hours at 60° C. Saturated sodium chloride solution was added to the mixture and the whole was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 0.16 g (60.7%) of the titled compound.

Workup

extractionthe whole was extracted with ethyl acetate
washThe organic layer was washed with saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customThe oily residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-163b2fcb18f54a529875c93288276c4a
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05547952

Reaction notes

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