tert-Butanol → HCID 66881539, compound

HRID 1893587Notes

Reaction equation

HRID 1893587 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:28])=[C:7]([N:9]([CH2:14][C:15]([N:17]([N:19]2[CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)[CH3:18])=[O:16])[CH2:10][C:11]([OH:13])=[O:12])[CH:8]=1)#[N:2].CCN=C=NCCCN(C)C.[C:40](O)([CH3:43])([CH3:42])[CH3:41]>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C.CCCCCC>[C:40]([O:12][C:11](=[O:13])[CH2:10][N:9]([C:7]1[CH:8]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=1[CH3:28])[CH2:14][C:15]([N:17]([N:19]1[CH2:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27]1)[CH3:18])=[O:16])([CH3:43])([CH3:42])[CH3:41]

Participants

7

Reactant 3

HCID 6386tert-ButanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66882037HCID 66882037, compound

Product 1

HCID 66881539HCID 66881539, compoundYield 74.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The compound (2.06 g, 5.44 mmol) of Example 1, step A, 4-dimethylaminopyridine (1.40 g, 11.5 mmol) and WSC (1.46 g, 7.62 mmol) were dissolved in dichloromethane (22 ml), tert-butanol (1.0 ml, 10 mmol) was added at room temperature, and the mixture was stirred at the same temperature overnight. The reaction mixture was diluted with an ethyl acetate-hexane=1:1 mixed solvent, and the organic layer was washed with 10% aqueous citric acid solution, water, diluted aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (1.76 g, yield 74%) as a colorless solid.

Workup

  1. washthe organic layer was washed with 10% aqueous citric acid solution, water, diluted aqueous sodium hydroxide solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe solution was concentrated under reduced pressure
  5. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-8511cc412701489ab8406b95cd88cbe1
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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