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Hydroxyamine hydrochloride → (+/-)-Isopropyl 5-[(3,5-bistrifluoromethyl-benzyl)-(5-methyl-isoxazol-5-yl)-amino]-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

HRID 507080
ノート
印刷プレビュー

反応式

HRID 507080 の反応式
Cl.[NH2:2]O.[C:4]([O-])(=O)[CH3:5].[Na+].[F:9][C:10]([F:48])([F:47])[C:11]1[CH:12]=[C:13]([CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1)[CH2:14][N:15]([C:34](=[O:39])[CH2:35]C(=O)C)[CH:16]1[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[C:18]2[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:17]1=2>CO>[F:47][C:10]([F:9])([F:48])[C:11]1[CH:12]=[C:13]([CH:40]=[C:41]([C:43]([F:44])([F:45])[F:46])[CH:42]=1)[CH2:14][N:15]([C:34]1([CH3:35])[O:39][NH:2][CH:4]=[CH:5]1)[CH:16]1[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[C:18]2[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:17]1=2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 59432322(+/-)-5-[(3,5-Bistrifluoromethyl-benzyl)-(3-oxo-butyryl)-amino]-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylic acid isopropyl ester

生成物 1

HCID 86615659(+/-)-Isopropyl 5-[(3,5-bistrifluoromethyl-benzyl)-(5-methyl-isoxazol-5-yl)-amino]-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate収率 797.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Add hydroxylamine hydrochloride (39 mg, 0.55 mmol) and sodium acetate (1.5 mg, 0.018 mmol). to a solution of compound (+/−)-5-[(3,5-bistrifluoromethyl-benzyl)-(3-oxo-butyryl)-amino]-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylic acid isopropyl ester (Example 51, Step 1) (218 mg, 0.37 mmol) in methanol (1.8 mL) at 0° C., Heat the reaction mixture under reflux overnight. Cool and remove the solvents under reduce pressure. Dilute the residue with ethyl acetate and brine. Separate the layers and dry the organic phase over magnesium sulfate, filter and concentrate in vacuo. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate to afford the title compound (85 mg, 39%). MS (ES+): 590 (M+H).

後処理

  1. temperatureunder reflux overnight
  2. temperatureCool
  3. customremove the solvents
  4. additionDilute the residue with ethyl acetate and brine
  5. customSeparate the layers
  6. dry with materialdry the organic phase over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify the residue by flash chromatography
  10. washeluting with hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-49edfeb8ef9049c48b2016b037b8289d
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07786108B2

反応ノート

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