Hydrochloric Acid → (R)-2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinimide

HRID 471356노트

반응식

HRID 471356 반응식
[C:1]([O:5][C:6]([NH:8][C@:9]([C:26](=[O:28])[NH2:27])([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:10][C:11](OCC1C=CC=CC=1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O.O>[C:1]([O:5][C:6]([NH:8][C@:9]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:10][C:11](=[O:12])[NH:27][C:26]1=[O:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66725258(R)-1-benzyl ethyl 3-t-butyloxycarbonylamino-3-carbamoylsuccinate

생성물 1

HCID 66725143(R)-2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinimide수율 90%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

(R)-1-Benzyl ethyl 3-t-butyloxycarbonylamino-3-carbamoylsuccinate (550 mg) obtained in Example 20 was dissolved in acetone (11 mL) and water (6 mL), the solution was added with potassium carbonate (231 mg), the mixture was stirred for 5 hours, and poured with 1 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography, in which elution was performed with n-hexane/ethyl acetate (1:1) for purification, and then recrystallized from ethyl acetate/n-hexane to obtain the title compound (358 mg, yield: 90%) as colorless crystals. Optical rotation [α]D25 was −29.5° (c 0.50, ethanol).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was subjected to silica gel column chromatography, in which elution
  6. customwas performed with n-hexane/ethyl acetate (1:1) for purification
  7. customrecrystallized from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-c6f838f1078a4d32bc0005c707517b29
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633001B2

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