Water → (S)-2-Acetylamino-4-dibenzofuran-2-yl-4-oxo-butyric acid

HRID 376405Notes

Reaction equation

HRID 376405 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]([C:9]1[CH:21]=[CH:20][C:12]2[O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:11]=2[CH:10]=1)=[O:8])[C:3]([OH:5])=[O:4].O.[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([NH:1][C@@H:2]([CH2:6][C:7]([C:9]1[CH:21]=[CH:20][C:12]2[O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:11]=2[CH:10]=1)=[O:8])[C:3]([OH:5])=[O:4])(=[O:25])[CH3:24]

Participants

4

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 53753679(S)-2-Amino-4-dibenzofuran-2-yl-4-oxo-butyric acid

Product 1

HCID 53666229(S)-2-Acetylamino-4-dibenzofuran-2-yl-4-oxo-butyric acid

Procedure

A suspension of (S)-2-amino-4-dibenzofuran-2-yl-4-oxo-butyric acid (0.025 g, 0.000082 mol) obtained above in Example 3 in acetic anhydride (2 mL) and water (4 mL) was sonicated (Cole Parmer 8850 Ultrasound Bath) for 15 minutes at room temperature. The resulting solution was then concentrated in vacuo, and the resulting residue was recrystallized from ethyl acetate/diethyl ether (50:50, v/v) to yield the title product as a white solid; mp 166-170° C.

Workup

  1. concentrationThe resulting solution was then concentrated in vacuo
  2. customthe resulting residue was recrystallized from ethyl acetate/diethyl ether (50:50

Sources & evidence

ORD record
ord-cc612f1cba554f73be4d2dd05f786133
Source dataset
uspto-grants-2000_02
Patent number
US06020366

Reaction notes

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