Hydrochloric Acid → 2-benzyl 3-tert-butyl (2RS,3RS)-5-oxotetrahydrofuran-2,3-dicarboxylate

HRID 1004342노트

반응식

HRID 1004342 반응식
[CH2:1]([O:8][C:9]([CH:11]1[CH:15]([C:16]([OH:18])=[O:17])[CH2:14][C:13](=[O:19])[O:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.[C:32](O)([CH3:35])([CH3:34])[CH3:33].Cl>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[O:19]=[C:13]1[O:12][CH:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH:15]([C:16]([O:18][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:17])[CH2:14]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18705291(2RS,3SR)-2-benzyloxycarbonyl-5-oxotetrahydrofuran-3-carboxylic acid

생성물 1

HCID 536709302-benzyl 3-tert-butyl (2RS,3RS)-5-oxotetrahydrofuran-2,3-dicarboxylate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6212Chloroform용매

실험 절차

7.93 g of (2RS,3SR)-2-(benzyloxycarbonyl)-5-oxotetrahydrofuran-3-carboxylic acid in 75 ml of chloroform was mixed with 5.5 g of 4-dimethylaminopyridine, 8.6 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 5.7 ml of tert-butyl alcohol successively and stirred at room temperature for 60 hours. The reaction solution was poured into 1N hydrochloric acid under cooling with ice and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1] to give 6.48 g of the title compound as a white solid.

후처리

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1]

출처 및 근거

ORD 기록
ord-2d7b9f88d9bd4414b7ac7d09154c5572
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048894

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