Dichloromethane methanol → HCID 87173151, compound

HRID 2041882Notes

Reaction equation

HRID 2041882 reaction equation
[CH3:1][N:2]([C@@H:10]([CH3:38])[C:11](=[O:37])[NH:12][C@@H:13]([CH2:34][C:35]#[CH:36])[C:14](=[O:33])[N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:32])[NH:21][C@H:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1)C(=O)OC(C)(C)C.CO.C(Cl)[Cl:42]>CC#N.CC([O-])=O.CC([O-])=O.[Cu+2]>[ClH:42].[CH3:1][NH:2][C@@H:10]([CH3:38])[C:11]([NH:12][C@@H:13]([CH2:34][C:35]#[CH:36])[C:14]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([NH:21][C@H:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1)=[O:32])=[O:33])=[O:37]

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 59512057HCID 59512057, compound

Product 1

HCID 87173151HCID 87173151, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

The title compound of Example 3 (600 mg, 1.14 mmol) and Cu(OAc)2 (1.05 g, 5.76 mmol) were dissolved in CH3CN (7.6 mL). This was refluxed for 20 mins. By TLC (10% MeOH/CH2Cl2), starting material was still present, so the mixture was refluxed for an additional 20 mins. By TLC, starting material had been consumed. Removed CH3CN via rotary evaporation and vacuum pump. Residue was then partitioned between ethyl acetate and water. Aqueous phase was discarded and organic phase was washed with brine and dried over Na2SO4. Oily residue was purified via flash column chromatography (a gradient of 100% ethyl acetate to 5% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2) to afford the title compound as a white solid. 1H NMR (CD3OH): consistent with proposed structure. MS (m/z): 1047.3.

Workup

  1. temperatureThis was refluxed for 20 mins
  2. temperaturewas refluxed for an additional 20 mins
  3. customhad been consumed
  4. customRemoved CH3CN via rotary evaporation and vacuum pump
  5. customResidue was then partitioned between ethyl acetate and water
  6. washorganic phase was washed with brine
  7. dry with materialdried over Na2SO4
  8. customOily residue was purified via flash column chromatography (a gradient of 100% ethyl acetate to 5% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-482eca4eed1641e1a53395f09bdd3401
Source dataset
uspto-grants-2013_11
Patent number
US08586542B2

Reaction notes

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