Dicyclohexylcarbodiimide → HCID 86598602、化合物

HRID 968527

反応式

HRID 968527 の反応式
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:15][CH2:14][S:13][CH2:12][C@H:11]2[C:16]([OH:18])=[O:17])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:20]1([CH:26](O)[CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:20]1([CH:26]([O:17][C:16]([C@@H:11]2[CH2:12][S:13][CH2:14][CH2:15][N:10]2[S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:19])=[CH:6][CH:5]=2)(=[O:9])=[O:8])=[O:18])[CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 2501291,3-Diphenylpropan-1-olHCID 69415969(3R)-4-(4-toluenesulfonyl)thiomorpholine-3-carboxylic acid

生成物 1

HCID 86598602HCID 86598602、化合物収率 30.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

0.301 g (1 mmol) of (3R)-4-(4-toluenesulfonyl)thiomorpholine-3-carboxylic acid, 0.318 g (1.5 mmol) of (1,3-diphenyl)-propanol, 0.088 g (0.33 mmol) of CAS, 0.227 g (1.2 mmol) of DCC and 0.04 g (0.33 mmol) of DMAP were dissolved in 15 mL of CH2Cl2. The mixture was stirred for 24 h at room temperature. The solid was filtrated and the solvent was evaporated. The residual was dissolved in a suitable amount of ethyl acetate (20 ml) and then the mixture was filtered to remove insoluble substance. The ethyl acetate was added to 60 ml and then the liquid was washed with 10% NaHCO3 solution, saturated NaCl solution and dried over Na2SO4. After the drying agent was removed and part of ethyl acetate was evaporated, the crude product was purified by flash column chromatography (eluent: ethyl acetate:cyclohexane=1:3) to obtain the product as a oil (0.15 g). 1H-NMR (400 MHz, CDCl3): δ 7.5040(d, 2H, J=8.32 Hz), 7.3751-7.0634 (m, 12H), 5.7186-5.6846 (m, 1H), 5.0645 (t, 1H, J=3.42 Hz), 4.0136-3.9800 (m, 1H), 3.4760-3.4052 (m, 1H), 3.1031-3.0773 (m, 2H), 2.8562-2.7914 (m, 1H), 2.6613-2.5414 (m, 2H), 2.4304-2.3855 (m, 1H), 2.3333 (s, 3H), 2.2283-2.2041 (m, 1H), 2.0565-2.0328 (m, 1H); MS (EI) m/z: 495.8, 449.8, 391.8, 339.8, 299.7, 255.7, 193.8, 154.8, 138.8, 116.9, 90.8, 64.9.

後処理

  1. filtrationThe solid was filtrated
  2. customthe solvent was evaporated
  3. dissolutionThe residual was dissolved in a suitable amount of ethyl acetate (20 ml)
  4. filtrationthe mixture was filtered
  5. customto remove insoluble substance
  6. additionThe ethyl acetate was added to 60 ml
  7. washthe liquid was washed with 10% NaHCO3 solution, saturated NaCl solution
  8. dry with materialdried over Na2SO4
  9. customAfter the drying agent was removed
  10. custompart of ethyl acetate was evaporated
  11. customthe crude product was purified by flash column chromatography (eluent: ethyl acetate:cyclohexane=1:3)

出典と根拠

ORDレコード
ord-1590aa3c784742268046c53c84aa3a03
出典データセット
uspto-grants-2007_12
特許番号
US07304057B2

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