Acetic Anhydride → N-(2-oxooxolan-3-yl)acetamide

HRID 1363639Notes

Reaction equation

HRID 1363639 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4]O.CN(C1C=CC=CN=1)C.[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[C:18]([NH:1][CH:2]1[CH2:3][CH2:4][O:7][C:6]1=[O:8])(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 12647L-HomoserineHCID 218852-Dimethylaminopyridine

Product 1

HCID 325257N-(2-oxooxolan-3-yl)acetamideYield 60%

Conditions

Temperature
60 °C

Procedure

L-Homoserine (2 mol) was suspended in 900 ml of acetic anhydride and admixed with a spatula tip full of dimethylaminopyridine (DMAP). It was slowly heated to 60° C. After approximately 1 hour, the temperature rapidly increased to 100° C. Subsequently the reaction mixture was stirred at 80° C. for 90 minutes and concentrated to dryness under vacuum. The resultant yellow oil was taken up in isopropanol (600 ml) and allowed to stand overnight at 0° C. The resultant crystals were filtered off, washed with cold isopropanol and dried under vacuum. The yield was 60% N-acetyl-2-amino-4-butyrolactone isolated, the purity 99% (according to HPLC).

Workup

  1. temperaturethe temperature rapidly increased to 100° C
  2. concentrationconcentrated to dryness under vacuum
  3. waitto stand overnight at 0° C
  4. filtrationThe resultant crystals were filtered off
  5. washwashed with cold isopropanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-a7305525f606492fae0a4b4643a085b6
Source dataset
uspto-grants-2011_02
Patent number
US07884240B2

Reaction notes

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