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

HRID 57754Notes

Reaction equation

HRID 57754 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-c7d2588b8770488eb71154d498eea4ee
Source dataset
uspto-grants-2016_09
Patent number
US09434737B2

Reaction notes

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