Isopropanol → HCID 67247965, compound

HRID 2425009Notes

Reaction equation

HRID 2425009 reaction equation
[CH2:1]1[CH2:6]CC(N=C=NC2CCCCC2)C[CH2:2]1.[C:16]([O:20][C:21]([NH:23][CH2:24][C:25]([C:27]1[CH:37]=[CH:36][C:30]([O:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:29][CH:28]=1)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].CC(O)C>CCOC(C)=O.CN(C1C=CN=CC=1)C>[CH:1]([O:34][C:33](=[O:35])[CH2:32][O:31][C:30]1[CH:29]=[CH:28][C:27]([C:25](=[O:26])[CH2:24][NH:23][C:21]([O:20][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:22])=[CH:37][CH:36]=1)([CH3:6])[CH3:2]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 10868DicyclohexylcarbodiimideHCID 54276808HCID 54276808, compound

Product 1

HCID 67247965HCID 67247965, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of DCC (2.06 g; 10 mmol) in EtOAc (10 ml) was added with stirring, at 0° C. to a mixture of the compound of example 1f (2.78 g; 9 mmol) and propane-2-ol (2 ml) in EtOAc (20 ml). DMAP (1.1 g; 9 mmol) was added after 10 min and stirring continued for 2 h at 0° C. The reaction mixture was stored in a freezer overnight. The precipitated DCU was filtered and the filtrate was washed with brine, dried (Na2SO4), concentrated and purified using flash chromatography (silica gel, 5% CH3CN in CHCl3) to obtain the title compound. Yield, 3.0 g (94.9%); mp, 62-64° C. (EtOAc-PE 60-80° C.); analysis: C18H25NO6 requires C, 61.53; H, 7.17; N, 3.99. found: C, 61.94; H, 7.19; N, 3.95%.

Workup

  1. waitThe reaction mixture was stored in a freezer overnight
  2. filtrationThe precipitated DCU was filtered
  3. washthe filtrate was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-7999ff3fa47d45bda53e0cf313f276ee
Source dataset
uspto-grants-2011_06
Patent number
US07964628B2

Reaction notes

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