Water → (2R)-2-amino-2-ethoxycarbonylsuccinimide

HRID 426023Notes

Reaction equation

C(OC([NH:11][C@:12]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][C:16](=[O:18])[NH:15][C:13]1=[O:14])=O)C1C=CC=CC=1.O.[H][H]>C(O)C.[Pd]>[NH2:11][C@:12]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][C:16](=[O:18])[NH:15][C:13]1=[O:14]

Participants

Conditions

Temperature: 35 °C

Procedure

(2R)-2-Benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide (24.4 g, 76.2 mmol) in ethanol (73.2 ml) was heated at 60° C. to be dissolved and 5% Pd—C (2.71 g) and water (2.17 g) were added at 30-40° C. of inner temperature. After the atmosphere was substituted with nitrogen gas, hydrogen gas was introduced and the mixture was stirred at 30-40° C. for about 33 hours. When completion of the reaction was confirmed by HPLC, the reaction solution was filtered, the insoluble materials were washed with sprayed ethanol (20 ml×2) and the filtrate was concentrated. The resulting crystals were recrystallized from ethanol (24.4 ml) and the precipitated crystals were filtered, washed with sprayed ethanol (15 ml) and dried in vacuo at room temperature to give (2R)-2-amino-2-ethoxycarbonylsuccinimide (12.3 g). Yield 86.7%, HPLC 99.7%, Optical purity 100% e.e.

Workup

dissolutionto be dissolved
additionwas introduced
filtrationthe reaction solution was filtered
washthe insoluble materials were washed with sprayed ethanol (20 ml×2)
concentrationthe filtrate was concentrated
customThe resulting crystals were recrystallized from ethanol (24.4 ml)
filtrationthe precipitated crystals were filtered
washwashed with sprayed ethanol (15 ml)
customdried in vacuo at room temperature

Sources & evidence

ORD record: ord-c45dc7e4037340778813a13426803f2c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106230B2

Reaction notes

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