Dicyclohexylcarbodiimide → 5-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 5581

反応式

HRID 5581 の反応式
[OH:1][CH:2]1[C:8]2[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=2[N:6]([C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][C:16]=2[O:31][CH3:32])[CH2:5][CH2:4][CH2:3]1.CN(C1C=CC=CN=1)C.Cl.CN(C1C=CC=CN=1)C.[C:53]([O:57][C:58]([NH:60][C@H:61]([C:66](O)=[O:67])[CH2:62][CH2:63][S:64][CH3:65])=[O:59])([CH3:56])([CH3:55])[CH3:54].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl.C(O)(=O)C.CO>[C:53]([O:57][C:58]([NH:60][C@H:61]([C:66]([O:1][CH:2]1[C:8]2[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=2[N:6]([C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][C:16]=2[O:31][CH3:32])[CH2:5][CH2:4][CH2:3]1)=[O:67])[CH2:62][CH2:63][S:64][CH3:65])=[O:59])([CH3:56])([CH3:55])[CH3:54]

参加物

9

反応物 5

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 89857Boc-L-methionineHCID 189174175-Hydroxy-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepineHCID 22461520Dimethylaminopyridine hydrochloride

生成物 1

HCID 228720795-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine収率 121.2%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 6212Chloroform溶媒

実験手順

5-Hydroxy-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.7 g), dimethylaminopyridine (0.83 g) and dimethylaminopyridine hydrochloride (0.72 g) are dissolved in chloroform (15 ml), and thereto are added N-tert-butoxycarbonyl-L-methionine (0.56 g) and dicyclohexylcarbodiimide (0.93 g), and the mixture is stirred at room temperature for 3 hours. To the mixture are added methanol (3 ml) and acetic acid (0.7 ml), and the mixture is stirred at room temperature for 30 minutes. The insoluble materials are removed by filtration, and to the filtrate is added 5% aqueous sodium hydrogen sulfate solution, and the mixture is extracted with dichloromethane. The dichloromethane layer is washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over magnesium sulfate. The solvent is evaporated and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=150:1) to give 5-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.27 g).

後処理

  1. stirringthe mixture is stirred at room temperature for 30 minutes
  2. customThe insoluble materials are removed by filtration
  3. additionto the filtrate is added 5% aqueous sodium hydrogen sulfate solution
  4. extractionthe mixture is extracted with dichloromethane
  5. washThe dichloromethane layer is washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent is evaporated
  8. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=150:1)

出典と根拠

ORDレコード
ord-c858891f9f9444f296084399c45e22a3
出典データセット
uspto-grants-1993_09
特許番号
US05244898

関連ノート

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