Benzyl chloroformate → ((Benzyloxy)carbonyl)-L-allothreonine

HRID 745128Notes

Reaction equation

HRID 745128 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C@H:13]([C:17]([OH:19])=[O:18])[C@H:14]([CH3:16])[OH:15].C([O-])(O)=O.[Na+]>O>[C:9]([NH:12][C@H:13]([C:17]([OH:19])=[O:18])[C@H:14]([CH3:16])[OH:15])([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 99289Allothreonine, L-HCID 516892Sodium Bicarbonate

Product 1

HCID 853483((Benzyloxy)carbonyl)-L-allothreonineYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzylchloroformate (0.35 ml; 2.3 mmol) was added to a mixture of L-allothreonine (0.25 g; 2.1 mmol) and NaHCO3 (435 mg; 5.18 mmol) in 2.5 ml of H2O at RT. After 3 h, the reaction mixture was partitioned between Et2O and H2O. The aqueous layer was washed with Et20, acidified to pH <2 with 6N HCl, and extracted with CH2Cl2. The organic layer was dried (MgSO4) and concentrated to afford 320 mg (63%) of Cbz-L-allothreonine.

Workup

  1. customthe reaction mixture was partitioned between Et2O and H2O
  2. washThe aqueous layer was washed with Et20
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-639c000f0e3b4bbf8fdebfdca5833985
Source dataset
uspto-grants-1996_09
Patent number
US05559256

Reaction notes

Loading…