Dicyclohexylcarbodiimide → HCID 69413498、化合物

HRID 968521

反応式

HRID 968521 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)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:31]([O:38][C:39](=[O:46])[C@H:40]([CH2:42][CH:43]([CH3:45])[CH3:44])[NH2:41])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:31]([O:38][C:39](=[O:46])[CH:40]([NH:41][C:16]([C@@H:11]1[CH2:12][S:13][CH2:14][CH2:15][N:10]1[S:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:19])=[CH:6][CH:5]=1)(=[O:8])=[O:9])=[O:18])[CH2:42][CH:43]([CH3:44])[CH3:45])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 6451312L-Leucine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)HCID 69415969(3R)-4-(4-toluenesulfonyl)thiomorpholine-3-carboxylic acid

生成物 1

HCID 69413498HCID 69413498、化合物収率 95.1%

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, 0.432 g (1.1 mmol) of L-leucine benzyl ester p-toluenesulfonic acid salt, 0.227 g (1.2 mmol) of DCC and 0.122 g (1 mmol) of DMAP were dissolved in 30 mL of CH2Cl2, 0.2 ml (1.4 mmol) of TEA was added. 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: CH2Cl2:CH3Cl=1:1) to obtain the product as a oil (0.48 g).

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: CH2Cl2:CH3Cl=1:1)

出典と根拠

ORDレコード
ord-6491c0af09824afeada9a5d22b83cb7f
出典データセット
uspto-grants-2007_12
特許番号
US07304057B2

関連ノート

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