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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
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HRID 1022705 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6cff76a331004cdda7b56db95b053b38
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722662B2

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