Trifluoroacetic acid → 5-(L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 5586

反応式

HRID 5586 の反応式
C(OC([NH:8][C@H:9]([C:14]([O:16][CH:17]1[C:23]2[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=2[N:21]([C:29](=[O:48])[C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:45])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[CH3:44])=[CH:32][C:31]=2[O:46][CH3:47])[CH2:20][CH2:19][CH2:18]1)=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=O)(C)(C)C.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[NH2:8][C@H:9]([C:14]([O:16][CH:17]1[C:23]2[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=2[N:21]([C:29](=[O:48])[C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:45])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[CH3:44])=[CH:32][C:31]=2[O:46][CH3:47])[CH2:20][CH2:19][CH2:18]1)=[O:15])[CH2:10][CH2:11][S:12][CH3:13]

参加物

4

反応物 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 228720795-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

生成物 1

HCID 228720785-(L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine収率 32.2%

実験手順

A uniform solution of 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), trifluoroacetic acid (2.5 ml) and anisole (0.6 ml) is stirred at room temperature for 2 hours. The trifluoroacetic acid is almost distilled off under reduced pressure, and the residue is acidified with an 0.2 N aqueous sodium hydroxide solution, and the mixture is extracted with dichloromethane. The dichloromethane layer is washed with water, dried over magnesium sulfate and concentrated. The resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate) to give Isomer A (0.34 g) and Isomer B (0.35 g) of 5-(L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine.

後処理

  1. distillationThe trifluoroacetic acid is almost distilled off under reduced pressure
  2. extractionthe mixture is extracted with dichloromethane
  3. washThe dichloromethane layer is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate)

出典と根拠

ORDレコード
ord-8b0e6b9d18174370a977ef82358fad31
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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