HCID 136396872, compound → HCID 136396995, compound

HRID 2110607Notes

Reaction equation

HRID 2110607 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>CC#N.O.[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 1

HCID 136396872HCID 136396872, compound

Product 1

HCID 136396995HCID 136396995, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of Example 83A (905 mg, 1.6 mmol) in CH3CN (72 mL) and H2O (5 mL) was added molybdenum hexacarbonyl (293 mg, 1.1 mmol) and the solution was refluxed for 2 hours, cooled to room temperature, solvent removed in vacuo and the crude residue purified by column chromatography on silica gel (2% methanol/chloroform) to give the title compound as a colorless solid (670 mg, 78%): 1H NMR (d6-DMSO) δ 14.34 (s, 1H), 9.64 (s, 1H), 8.59 (br s, 2H), 8.13, 8.11 (d, 1H), 7.93 (s, 1H), 7.69-7.45 (m, 4H), 7.27, 7.24 (d, 1H), 2.08-1.95 (m, 1H), 1.92-1.80 (m, 1H), 1.30-0.99 (m, 4H), 0.54-0.46 (m, 1H), 1.50 (s, 9H), 1.45-1.23 (m, 1H), 1.18-0.96 (m, 1H), 0.92-0.62 (m, 7H); MS (ESI) m/z 541 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-cf261c2465234c36a29d90e0f55ddc6b
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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