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Benzyl chloroformate → HCID 86691270, 화합물

HRID 2037296
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HRID 2037296 반응식
Cl.[CH2:2]([O:4][C:5]([C@:7]1([NH2:19])[CH2:12][C:11](=[O:13])[C@@H:10]2[C@H:8]1[C@H:9]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:6])[CH3:3].C(=O)([O-])[O-].[K+].[K+].Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>O1CCCC1.C(OCC)(=O)C.O>[CH2:30]([O:29][C:27]([NH:19][C@@:7]1([C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH2:12][C:11](=[O:13])[C@@H:10]2[C@H:8]1[C@H:9]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
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참가 물질

7

반응물 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 86691271HCID 86691271, 화합물

생성물 1

HCID 86691270HCID 86691270, 화합물수율 99%

시약·촉매·용매 3

HCID 962Water용매2회HCID 8028Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

실험 절차

Suspend diethyl-(1S,2S,5R,6R)-2-amino-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate-hydrochloride (55.0 g, 188.5 mmol) in tetrahydrofuran (220 mL), then add water (220 mL) and potassium carbonate (92.1 g, 659.9 mmol). Stir the resulting mixture for 30 minutes. Add benzyl chloroformate (26.7 mL, 175.3 mmol) to the mixture over 45 minutes, keeping the reaction temperature below 25° C. Stir reaction mixture for 30 minutes, then dilute with ethyl acetate (550 mL) and water (275 mL). Separate the phases and back extract the aqueous layer with ethyl acetate (250 mL). Combine the organics and wash it sequentially with aqueous HCl (0.5N, 100 mL), saturated NaHCO3 (100 mL) and brine (100 mL). Dry the organic solution over Na2SO4, filter and concentrate in vacuo to afford the title compound as a clear oil (67.6 g, 92.1%). 1H NMR (CDCl3) δ 1.24-1.26 (m, 6H), 2.36 (bs, 1H), 2.47 (dd, 1H), 2.78 (dd, 1H), 2.90 (dd, 1H), 4.09-4.19 (m, 4H), 5.08 (s, 2H), 5.73 (s, 1H), 7.24-7.36 (m, 5H).

후처리

  1. customthe reaction temperature below 25° C
  2. stirringStir
  3. customreaction mixture for 30 minutes
  4. customSeparate the phases
  5. extractionback extract the aqueous layer with ethyl acetate (250 mL)
  6. washCombine the organics and wash it sequentially with aqueous HCl (0.5N, 100 mL), saturated NaHCO3 (100 mL) and brine (100 mL)
  7. dry with materialDry the organic solution over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

출처 및 근거

ORD 기록
ord-73ad15fa74764bb68a9f8594dd875b65
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08575214B2

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