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

HRID 57741Notes

Reaction equation

HRID 57741 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>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

4

Reactant 1

HCID 9944916(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide

Product 1

HCID 10679104(2R)-2-amino-2-ethoxycarbonylsuccinimideYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(R)-2-Benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide (80 mg) was dissolved in ethanol (10 mL), the solution was added with 5% palladium/carbon (4 mg), and catalytic hydrogenation was performed at room temperature under a hydrogen atmosphere. After the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethanol to obtain the title compound (43 mg, yield: 93%) as colorless crystals. Optical rotation [α]D24 was −35.9° (c 0.22, ethanol). Optical purity was more than 99.9% ee.

Workup

  1. customwas performed at room temperature under a hydrogen atmosphere
  2. customAfter the catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-41cbebabc8ef4ba4bfe519bc0a19195d
Source dataset
uspto-grants-2016_09
Patent number
US09434737B2

Reaction notes

Loading…