L-Homoserine → Cbz-L-Homoserine

HRID 2085929Notes

Reaction equation

HRID 2085929 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].[CH2:9]([O:16][C:17](ON1C(=O)CCC1=O)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C>[CH2:9]([O:16][C:17]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 12647L-HomoserineHCID 83172Benzyl succinimido carbonate

Product 1

HCID 489187Cbz-L-Homoserine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

6 g (50.4 mmol) of L-homoserine were largely dissolved in 50 ml of DMF and treated at 0° C. in portions with 12.56 9 (50.4 mmol) of N-(benzyloxycarbonyloxy)succinimide. The mixture was stirred at 0° C. for 1 h, then at RT for 48 h. The solvent was distilled off and the residue was partitioned between EA and a saturated NaCl solution. The organic phase was washed with saturated NaCl solution, with 5% strength citric acid and again with saturated NaCl solution, dried, filtered and concentrated. The crystalline residue was stirred in ether, filtered off with suction, and washed with ether and pentane. Yield: 9.55 g (75%).

Workup

  1. waitat RT for 48 h
  2. distillationThe solvent was distilled off
  3. customthe residue was partitioned between EA
  4. washThe organic phase was washed with saturated NaCl solution, with 5% strength citric acid and again with saturated NaCl solution
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. stirringThe crystalline residue was stirred in ether
  9. filtrationfiltered off with suction
  10. washwashed with ether and pentane

Sources & evidence

ORD record
ord-36f933081ae84da888207b3c96ca8385
Source dataset
uspto-grants-2004_04
Patent number
US06723727B1

Reaction notes

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