Sulfuric Acid → HCID 135885187, compound

HRID 2110599Notes

Reaction equation

HRID 2110599 reaction equation
[CH3:1][C:2]([CH3:36])([CH3:35])[CH2:3][CH2:4][C:5]1(O)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][C:19]=3[S:18](=[O:32])(=[O:31])[N:17]=2)[C:6]1=[O:33].[OH:37]S(O)(=O)=O.[CH3:42][C:43]#[N:44]>>[CH3:36][C:2]([CH3:1])([CH3:35])[CH2:3][CH2:4][C:5]1([NH:44][C:43](=[O:37])[CH3:42])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:25][C:19]=3[S:18](=[O:32])(=[O:31])[N:17]=2)[C:6]1=[O:33]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 135885141HCID 135885141, compound

Product 1

HCID 135885187HCID 135885187, compoundYield 88%

Procedure

To a solution of the product from Example 8F (20 mg, 38 μmol) in CH3CN (0.2 mL) at 0° C. was added conc. H2SO4 (0.2 mL) dropwise. The resulting mixture was stirred at room temperature for 3 h and was poured onto ice (˜5 mL). The mixture was allowed to warm to room temperature, and the product was collected by filtration to give the title compound as an off-white solid (19 mg, 88%). 1H NMR (300 MHz, DMSO-d6) δ ppm 13.65 (br s, 1H), 10.26 (s, 1H), 9.15 (s, 1H), 8.12 (d, J=7.0 Hz, 1H), 7.69-7.79 (m, 2H), 7.47-7.65 (m, 4H), 3.06 (s, 3H), 2.50 (s, 3H), 1.74-2.06 (m, 2H), 0.84-1.00 (m, 1H), 0.66 (s, 9H), 0.39-0.58 (m, 1H).

Workup

  1. additionwas poured onto ice (˜5 mL)
  2. temperatureto warm to room temperature
  3. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-97fdaa3fb48e414fabedaa7406a4d590
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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