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

HRID 962656Notes

Reaction equation

HRID 962656 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 Et2O, acidified to pH <2 with 6N HCl, and extracted with CH2 Cl2. 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 Et2O
  3. extractionextracted with CH2 Cl2
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ff152904544448a8a1006271d84d3929
Source dataset
uspto-grants-1998_06
Patent number
US05760036

Reaction notes

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