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Hydrochloric Acid → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-(4-ethoxy-2,4-dioxobutyl)-1,4-oxazepane-4-carboxylate

HRID 1022705
ノート
印刷プレビュー

反応式

HRID 1022705 の反応式
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]([O:17][C:18]([N:20]1[CH2:26][C@@H:25]([CH2:27][C:28]([OH:30])=O)[C@H:24]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=2)[O:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH2:39]([O:41][C:42](=[O:47])[CH2:43]C([O-])=O)[CH3:40].[K+].[Cl-].[Mg+2].[Cl-].Cl>C1COCC1>[Cl:38][C:33]1[CH:32]=[C:31]([C@@H:24]2[O:23][CH2:22][CH2:21][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:26][C@H:25]2[CH2:27][C:28](=[O:30])[CH2:43][C:42]([O:41][CH2:39][CH3:40])=[O:47])[CH:36]=[CH:35][C:34]=1[Cl:37]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium ChlorideHCID 66976505[(6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl]acetic acid

生成物 1

HCID 66976292
tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-(4-ethoxy-2,4-dioxobutyl)-1,4-oxazepane-4-carboxylate
収率 87.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

CDI (0.991 g, 6.11 mmol) was added to a solution of [(6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl]acetic acid (1.9 g, 4.70 mmol) in THF (20 ml), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were added potassium 3-ethoxy-3-oxopropanoate (0.880 g, 5.17 mmol) and magnesium chloride (0.492 g, 5.17 mmol). The reaction mixture was stirred at 60° C. for 5 hr. To the reaction mixture was added 1 N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (1.959 g).

後処理

  1. stirringThe reaction mixture was stirred at 60° C. for 5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-6cff76a331004cdda7b56db95b053b38
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722662B2

反応ノート

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