Dicyclohexylcarbodiimide → HCID 66933378, compound

HRID 855490Notes

Reaction equation

HRID 855490 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH3:14])=[CH:10][C:11]([OH:13])=O.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[CH3:40][C:41]1([CH2:47][CH2:48][C:49]2[C:54]([CH3:56])([CH3:55])[CH2:53][CH2:52][CH2:51][C:50]=2[CH3:57])[NH:46][CH2:45][CH2:44][CH2:43][O:42]1>C1COCC1.CN(C1C=CN=CC=1)C>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH3:14])=[CH:10][C:11]([N:46]1[CH2:45][CH2:44][CH2:43][O:42][C:41]1([CH3:40])[CH2:47][CH2:48][C:49]1[C:54]([CH3:56])([CH3:55])[CH2:53][CH2:52][CH2:51][C:50]=1[CH3:57])=[O:13]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 21947127HCID 21947127, compoundHCID 66933108HCID 66933108, compound

Product 1

HCID 66933378HCID 66933378, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 11.1 g (0.050 mol) of 3-(2,4-dihydroxy-phenyl)-3-methyl-acrylic acid in 500 mL of anhydrous THF is added 10.3 g (0.050 mol) of DCC. After stirring for 10 min, 6.8 g (0.050 mol) of HOBt, 11.3 g (0.045 mol) of 2-methyl-2-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-ethyl]-[1,3]oxazinane (8) and 1.1 g (0.009 mol) of DMAP are added and stirred at 0° C. for 1 h, warmed to room temperature and stirred for an additional 24 h. The mixture is cooled to 0° C., filtered and the solvent is removed in vacuo. The residue is diluted with ethyl acetate and washed three times with saturated sodium bicarbonate, followed by 10% citric acid and brine. The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The product 9 is further purified by flash chromatography on basic alumina with 20:1 chloroform/methanol.

Workup

  1. stirringstirred at 0° C. for 1 h
  2. stirringstirred for an additional 24 h
  3. temperatureThe mixture is cooled to 0° C.
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo
  6. additionThe residue is diluted with ethyl acetate
  7. washwashed three times with saturated sodium bicarbonate
  8. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe product 9 is further purified by flash chromatography on basic alumina with 20:1 chloroform/methanol

Sources & evidence

ORD record
ord-2243dd92cbd74c80a74012455412a1a9
Source dataset
uspto-grants-2007_08
Patent number
US07262156B2

Reaction notes

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