DL-Serine → HCID 10955823, compound

HRID 1864364Notes

Reaction equation

HRID 1864364 reaction equation
[NH2:1][CH:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[OH-].[Na+]>[C:8]1([S:14]([NH:1][CH:2]([CH2:3][OH:4])[C:5]([OH:7])=[O:6])(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 617DL-SerineHCID 7369Benzenesulfonyl chloride

Product 1

HCID 10955823HCID 10955823, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

DL-serine (1.051 g) was dissolved in a 1 M aqueous NaOH solution (20 ml). Benzenesulfonyl chloride (1.77 g) was added at 0° C. After 30 min the ice bath was removed and the mixture was stirred for 18 h at room temperature. The mixture was again placed in an ice bath. The mixture was acidified to pH 1 using 25% aqueous HCl. The colorless precipitate was collected by filtration, washed with 1 M HCl and dried to give (RS)-2-benzenesulfonylamino-3-hydroxy-propionic acid (1.23 g) as a colorless solid.

Workup

  1. customAfter 30 min the ice bath was removed
  2. customThe mixture was again placed in an ice bath
  3. filtrationThe colorless precipitate was collected by filtration
  4. washwashed with 1 M HCl
  5. customdried

Sources & evidence

ORD record
ord-4420a3142cc748e58ae2afd983ef41e6
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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