Tetrahydrofuran → HCID 86601812, compound

HRID 227482Notes

Reaction equation

HRID 227482 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH2:13])=[O:12])=[C:5]2[S:14]([N:17]1[C:21](O)=[CH:20][CH:19]=[C:18]1O)(=[O:16])=[O:15].ClC1C=C(C=CC=1)C(OO)=[O:29].O1CCCC1>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH2:13])=[O:12])=[C:5]2[S:14]([N:17]1[CH2:18][C@@H:19]2[C@@H:20]([O:29]2)[CH2:21]1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 70297m-Chloroperbenzoic acid3×HCID 68444340HCID 68444340, compound

Product 1

HCID 86601812HCID 86601812, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirring suspension of 5-bromo-3-(2,5-dihydroxy-1H-pyrrol-1-ylsulfonyl)-1H-indole-2-carboxamide (10 mg, 0.027 mmol, 1.0 equiv.) in 2 mL of acetone was added m-chloroperoxybenzoic acid (6.5 mg, 0.038 mmol, 1.4 equiv.). After stirring for 3 hours, 3 mL of tetrahydrofuran and m-chloroperoxybenzoic acid (6.5 mg, 0.038 mmol, 1.4 equiv.) were added. After stirring an additional 72 hours, more m-chloroperoxybenzoic acid (13 mg, 0.076 mmol, 2.8 equiv.) was added and, after 3 hours, the solvent was removed in vacuo. The title compound was obtained after purification by preparative reversed phase HPLC. Proton NMR for the product was consistent with the titled compound. ESI+MS: 385.96 [M+H]+.

Workup

  1. stirringAfter stirring an additional 72 hours
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-531995957b374752b1ef03c844259962
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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