Benzyl chloroformate → Z-D-Ser-OH

HRID 1401874Notes

Reaction equation

HRID 1401874 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
2.5 °C

Procedure

Sodium bicarbonate (240 g) was added to a mixture of D-serine (100 g) and water (800 ml) at 0-5° C. Benzylchloroformate (50% solution in toluene)(480 ml) was added to the reaction mixture and stirred for 10 hours at 0-5° C. The organic and aqueous layers were separated and washed the aqueous layer with toluene. Aqueous layer pH was adjusted to 1.5 with hydrochloric acid and extract the reaction mixture in to ethyl acetate. Distilled off the solvent from the extracted reaction mixture under reduced pressure to get the title compound.

Workup

  1. customThe organic and aqueous layers were separated
  2. washwashed the aqueous layer with toluene
  3. extractionextract the reaction mixture in to ethyl acetate
  4. distillationDistilled off the solvent
  5. customfrom the extracted reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-c7b47e29e9514fa49f40ab4c87c04cfd
Source dataset
uspto-grants-2014_12
Patent number
US08907132B2

Reaction notes

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