Sulfuric Acid → HCID 22558811, compound

HRID 2378563Notes

Reaction equation

NC(N)=[S:3].S(=O)(=O)(O)O.Br[C:11]1[S:12][C:13]2[CH:19]=[C:18]([C:20]3[CH:21]=[C:22]([CH2:34][CH2:35][C:36]([O:38]CC)=[O:37])[CH:23]=[CH:24][C:25]=3[O:26][CH2:27][CH:28]3[CH2:33][CH2:32][CH2:31]C[CH2:29]3)[CH:17]=[CH:16][C:14]=2[N:15]=1.[OH-].[Na+]>C(#N)C.O>[CH:28]1([CH2:27][O:26][C:25]2[CH:24]=[CH:23][C:22]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[CH:21][C:20]=2[C:18]2[CH:17]=[CH:16][C:14]3[NH:15][C:11](=[S:3])[S:12][C:13]=3[CH:19]=2)[CH2:33][CH2:32][CH2:31][CH2:29]1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution obtained beforehand by adding thiourea (52 mg, WAKO) to 1 M sulfuric acid (5 ml) and mixing them was added with a solution of Intermediate 76 (101 mg) in acetonitrile (5 ml), and stirred at 90° C. for 20 hours. The reaction mixture was poured into water (20 ml), neutralized by addition of 1 N aqueous sodium hydroxide under ice cooling, and then extracted with ethyl acetate (80 ml×3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, methylene chloride:ethanol=30:1) to obtain the title compound (Compound No. V-91, 46 mg).

Workup

customA solution obtained
additionmixing them
extractionextracted with ethyl acetate (80 ml×3)
washThe organic layer was washed with saturated brine
customdried
customthe solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography (Quad, methylene chloride:ethanol=30:1)

Sources & evidence

ORD record: ord-7515e042696c46fca40fb4638c9d5222
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470807B2

Reaction notes

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