N-[N-(tert-Butoxycarbonyl)-O-benzyl-L-seryl]-D-leucine methyl ester → HCID 54521511, compound

HRID 2271001Notes

Reaction equation

HRID 2271001 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C@@H:4]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH:5][C:6](=[O:25])[C@H:7]([CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:8][C:9](OC(C)(C)C)=O>Cl.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:30])[C@@H:4]([CH2:26][CH:27]([CH3:28])[CH3:29])[NH:5][C:6](=[O:25])[C@H:7]([CH2:16][O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH:8][CH2:9][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 1

HCID 54078518N-[N-(tert-Butoxycarbonyl)-O-benzyl-L-seryl]-D-leucine methyl ester

Product 1

HCID 54521511HCID 54521511, compoundYield 141.3%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

N-[N-(tert-Butoxycarbonyl)-O-benzyl-L-seryl]-D-leucine methyl ester (545 mg) was dissolved in 4N HCl-AcOEt (5 ml), and the solution was stirred at ambient temperature for 1.5 hours. The solvent was evaporated in vacuo. The resulting oil was dissolved in dry MeOH (5 ml). Benzaldehyde (205 mg) and sodium cyanoborohydride (NaBH3CN, 97 mg) were added to this solution, and the reaction mixture was stirred at ambient temperature for 3 hours. Benzaldehyde (60 mg) and NaBH3CN (30 mg) were added to the reaction mixture and the mixture was stirred at ambient temperature for 1.5 hours. After evaporation of the solvent in vacuo, the residue was partitioned by dissolving same in AcOEt and saturated aqueous NaHCO3 solution. The organic layer was washed with saturated sodium chloride (NaCl) solution, dried over MgSO4, and concentrated in vacuo. The residue was purified by SiO2 column chromatography (eluent: CHCl3) to give 376 mg of N-(N,O-dibenzyl-L-seryl)-D-leucine methyl ester as an oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe resulting oil was dissolved in dry MeOH (5 ml)
  3. additionBenzaldehyde (205 mg) and sodium cyanoborohydride (NaBH3CN, 97 mg) were added to this solution
  4. stirringthe reaction mixture was stirred at ambient temperature for 3 hours
  5. additionBenzaldehyde (60 mg) and NaBH3CN (30 mg) were added to the reaction mixture
  6. stirringthe mixture was stirred at ambient temperature for 1.5 hours
  7. customAfter evaporation of the solvent in vacuo
  8. customthe residue was partitioned
  9. dissolutionby dissolving same in AcOEt
  10. washThe organic layer was washed with saturated sodium chloride (NaCl) solution
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by SiO2 column chromatography (eluent: CHCl3)

Sources & evidence

ORD record
ord-33d5ed4833bd49c6b600c15fd984dc0e
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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