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

HRID 471356ノート

反応式

HRID 471356 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 66725143(R)-2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinimide収率 90%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-c6f838f1078a4d32bc0005c707517b29
出典データセット
uspto-grants-2014_01
特許番号
US08633001B2

反応ノート

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