Acetic Anhydride → N-Acetyl-D-serine

HRID 1401871Notes

Reaction equation

HRID 1401871 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11]>C(O)(=O)C>[C:1]([NH:8][C@H:9]([CH2:10][OH:11])[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 71077D-Serine

Product 1

HCID 10844522N-Acetyl-D-serine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
30 °C

Procedure

Acetic anhydride (10.79 ml) was added to a suspension of D-serine (10 grams) in acetic acid (150 ml) and stirred at 25-35° C. After completion of the reaction, acetic acid was removed by distillation followed by co-distillation with tetrahydrofuran. Isopropyl alcohol (30 ml) and methyltertiarybutylether (60 ml) was added to the obtained residue and stirred for 30 minutes. The obtained solid was filtered off and then solvent from the filtrate was distilled off completely under reduced pressure to get the title compound.

Workup

  1. customwas removed by distillation
  2. additionIsopropyl alcohol (30 ml) and methyltertiarybutylether (60 ml) was added to the obtained residue
  3. stirringstirred for 30 minutes
  4. filtrationThe obtained solid was filtered off
  5. distillationsolvent from the filtrate was distilled off completely under reduced pressure

Sources & evidence

ORD record
ord-9d54cf5e610641f7a3a547dc6b7b364b
Source dataset
uspto-grants-2014_12
Patent number
US08907132B2

Reaction notes

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