Benzyl chloroformate → Z-D-Ser-OH

HRID 1401875Notes

Reaction equation

HRID 1401875 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C@@H:7]([C:10]([OH:12])=[O:11])[CH2:8][OH:9].[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[CH2:13]([O:20][C:21]([NH:6][C@@H:7]([C:10]([OH:12])=[O:11])[CH2:8][OH:9])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 71077D-SerineHCID 516892Sodium Bicarbonate

Product 1

HCID 489184Z-D-Ser-OH

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
17.5 °C

Procedure

Sodium bicarbonate (60 g) was added to a mixture of D-serine (25 g) and water (375 ml) at 15-20° C. Benzylchloroformate (50% solution in toluene)(120 ml) was added slowly to the reaction mixture and stirred for 10 hours at 15-20° C. Filtered the reaction mixture and the filtrate was taken. The organic and aqueous layers were separated and washed the aqueous layer with methylene chloride. Aqueous layer pH was adjusted to 1.5 with hydrochloric acid. Stirred the reaction mixture for 90 minutes. Filtered the solid and washed with water. Dried the material to get the title compound.

Workup

  1. filtrationFiltered the reaction mixture
  2. customThe organic and aqueous layers were separated
  3. washwashed the aqueous layer with methylene chloride
  4. stirringStirred the reaction mixture for 90 minutes
  5. filtrationFiltered the solid
  6. washwashed with water
  7. customDried the material

Sources & evidence

ORD record
ord-6e2841112e874b2d9a729d69db4bf8f7
Source dataset
uspto-grants-2014_12
Patent number
US08907132B2

Reaction notes

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