Acetic Anhydride → N-Acetyl-D-serine

HRID 1401873Notes

Reaction equation

HRID 1401873 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@H:9]([CH2:13][OH:14])[C:10]([OH:12])=[O:11]>C(O)(=O)C>[C:1]([NH:8][C@H:9]([CH2:13][OH:14])[C:10]([OH:12])=[O:11])(=[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
32.5 °C

Procedure

Acetic anhydride (23.4 ml) was added to the suspension of (R)-2-amino-3-hydroxypropanoic acid compound of formula-3 (20 grams) in acetic acid (300 ml) and stirred for 24 hours at 30-35° C. After completion of the reaction, acetic acid was removed by distillation followed by co-distillation with tetrahydrofuran. Isopropyl alcohol (60 ml) and methyltertiarybutylether (120 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 (60 ml) and methyltertiarybutylether (120 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-1527d0c2ec9c4fb6a7de60d6d9135503
Source dataset
uspto-grants-2014_12
Patent number
US08907132B2

Reaction notes

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