Water → HCID 135885150, compound

HRID 2110584Notes

Reaction equation

HRID 2110584 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:17]OC)([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:4](=[O:20])[C:3]=1[C:21]1[NH:26][C:25]2[CH:27]=[CH:28][C:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][C:24]=2[S:23](=[O:40])(=[O:39])[N:22]=1.O>CC#N.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[NH2:17][C:5]1([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:21]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][C:24]=3[S:23](=[O:40])(=[O:39])[N:22]=2)[C:4]1=[O:20]

Participants

5

Reactant 2

HCID 962WaterHCID 135885149HCID 135885149, compound

Product 1

HCID 135885150HCID 135885150, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of Example 18B (205 mg, 0.36 mol) in CH3CN (16 mL) was added H2O (1.1 mL) and molybdenum hexacarbonyl (66 mg, 0.25 mol) and the solution was refluxed for 2 hours. After cooling to room temperature the solvent was removed in vacuo and the crude product was purified by column chromatography on silica gel (3% methanol/chloroform) to give the title compound as a colorless solid (163 mg, 81%): 1H NMR (d6-dmso) δ 14.34 (s, 1H), 9.64 (s, 1H), 8.59 (br s, 2H), 8.13, 8.11 (d, 1H), 7.94 (s, 1H), 7.71-7.49 (m, 4H), 7.27, 7.24 (d, 1H), 2.06-1.96 (m, 1H), 1.91-1.81 (m, 1H), 1.50 (s, 9H), 1.42-1.18 (m, 1H), 1.18-0.94 (m, 1H), 0.75-0.66 (m, 6H), 0.66-0.59 (m, 1H); MS (ESI) m/z 541 (M+H+).

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. customwas removed in vacuo
  3. customthe crude product was purified by column chromatography on silica gel (3% methanol/chloroform)

Sources & evidence

ORD record
ord-e431c66552e844cf8cb1c03db56fc978
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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