3-Benzyloxycarbonylamino-succinamic acid tert-butyl ester → L-Aspartic alpha-amide beta-t-butyl ester

HRID 1814343Notes

Reaction equation

HRID 1814343 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][CH:8]([NH:12]C(OCC1C=CC=CC=1)=O)[C:9]([NH2:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[C:1]([O:5][C:6](=[O:23])[CH2:7][C@H:8]([NH2:12])[C:9]([NH2:11])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 27287123-Benzyloxycarbonylamino-succinamic acid tert-butyl ester

Product 1

HCID 7019655L-Aspartic alpha-amide beta-t-butyl esterYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution 3-benzyloxycarbonylamino-succinamic acid tert-butyl ester (5.0 g, 15.50 mmol) in THF (20 mL) was added 20% Pd/C (150 mg), and the mixture was stirred for 4 h under H2 atmosphere at 50 psi. The catalyst was filtered and the solvent removed. The resulting oil solidifies upon the addition of ether. The solid was dried to give 2.90 g (98%) of (S)-3-amino-succinamic acid tert-butyl ester as an off white solid. The solid was used immediately in the next step. MS (APCI) m/z 189.1 (M+1).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent removed
  3. additionThe resulting oil solidifies upon the addition of ether
  4. customThe solid was dried

Sources & evidence

ORD record
ord-55666ac790f74d9da1fca00e75408015
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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