Dicyclohexylcarbodiimide → HCID 66933378、化合物

HRID 2214343ノート

反応式

HRID 2214343 の反応式
[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]

参加物

7

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 21947127HCID 21947127、化合物HCID 66933108HCID 66933108、化合物

生成物 1

HCID 66933378HCID 66933378、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4286200470d04541b27eff8dbc171045
出典データセット
uspto-grants-2006_09
特許番号
US07109153B2

反応ノート

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