Benzyl chloroformate → Cbz-L-Homoserine

HRID 1896152Notes

Reaction equation

HRID 1896152 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]>O1CCOCC1>[CH2:13]([O:12][C:10]([NH:1][C@@H:2]([CH2:3][CH2:4][OH:5])[C:6]([OH:8])=[O:7])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 12647L-Homoserine

Product 1

HCID 489187Cbz-L-Homoserine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To an ice-cooled solution of H-Hse-OH (3 g) in dioxane/2M NaOH (100 mL/25 mL) was added benzyl chloroformate (4 mL) dropwise over 15 min. The reaction mixture was allowed to warm to RT and was stirred overnight at RT. The solvent was evaporated off and the aq. residue was extracted with Et2O and acidified with a 2M HCl solution. The aq. phase was extracted with DCM. The DCM layers were combined, dried (Na2SO4) and evaporated off to give the desired product as a white powder (4.13 g).

Workup

  1. customThe solvent was evaporated off
  2. extractionthe aq. residue was extracted with Et2O
  3. extractionThe aq. phase was extracted with DCM
  4. dry with materialdried (Na2SO4)
  5. customevaporated off

Sources & evidence

ORD record
ord-40f9dd42c24a4dfd8e12540fc7d79ef5
Source dataset
uspto-grants-2013_08
Patent number
US08518912B2

Reaction notes

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