Water → 3-Hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acid

HRID 852538Notes

Reaction equation

N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=1)[C:5]([OH:7])=[O:6].[N-]=[N+]=[N-].[Na+].[OH2:21]>Cl.CO.CCOC(C)=O>[OH:21][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (D6) (280 mg, 1.25 mmol, 1 equiv) in a mixture of 2N aqueous HCl solution (2.5 ml) and MeOH (5 ml) at 0° C. was added NaN3 (190 mg, 2.75 mmol, 2.2 equiv) portionwise over 20 min. H2O (5 ml) was added and the resulting mixture was heated at 90° C. for 1 h then cooled to room temperature and diluted with AcOEt. The two layers were separated and the aqueous phase was extracted twice with AcOEt (20 ml). The combined organic layers were washed with brine (20 ml), dried over MgSO4 and concentrated in vacuo to give a crude product which was triturated with Et2O/MeOH to give 3-hydroxy-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (D36) (110 mg, 40%) as a light tan solid.

Workup

temperaturethen cooled to room temperature
customThe two layers were separated
extractionthe aqueous phase was extracted twice with AcOEt (20 ml)
washThe combined organic layers were washed with brine (20 ml)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give a crude product which
customwas triturated with Et2O/MeOH

Sources & evidence

ORD record: ord-5408c3f45b9a43209ab9266743c58665
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253198B2

Reaction notes

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