Dicyclohexylcarbodiimide → HCID 66933378, 화합물

HRID 1611235노트

반응식

HRID 1611235 반응식
[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]

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 21947127HCID 21947127, 화합물HCID 66933108HCID 66933108, 화합물

생성물 1

HCID 66933378HCID 66933378, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e4917554c1ed4a33a75cf611f830a141
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06987084B2

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