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

반응식

HRID 5581 반응식
[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]

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c858891f9f9444f296084399c45e22a3
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244898

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