Sodium Hydroxide → (8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)acetic acid sodium salt hydrate

HRID 2255481Notes

Reaction equation

HRID 2255481 reaction equation
CC([O:5][C:6](=[O:19])[CH2:7][N:8]1[CH2:16][CH2:15][CH2:14][NH:13][C:12]2[C:11](=[O:17])[C:10](=[O:18])[C:9]1=2)(C)C.[OH-].[Na+:21]>>[OH2:5].[Na+:21].[O:17]=[C:11]1[C:10](=[O:18])[C:9]2[N:8]([CH2:7][C:6]([O-:19])=[O:5])[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=2

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 10635453(8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)acetic acid 1,1-dimethylethyl ester

Product 1

HCID 131717663(8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)acetic acid sodium salt hydrateYield 132.9%

Procedure

An ethanolic (86 mL) solution of (8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)acetic acid 1,1-dimethylethyl ester (2.29 g, 8.60 mmol) was treated at room temperature with 2.5N sodium hydroxide solution (3.5 mL, 8.7 mmol) and left stirring overnight. The suspension was filtered, washing with ethyl acetate to give a solid which was recrystallized from methanol/water/isopropanol (final volume 50 mL) to afford (8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)acetic acid sodium salt hydrate (1.43 g, 66%, mp 280°-300° C. dec); MS (-FAB): 231 (M-H, 37), 209 (M-Na, 100); 1H NMR (DMSO 1 drop of DCl, 400 MHz): δ 4.40 (s, 2H), 3.36-3.25 (m, 4H), 1.89 (m, 2H).

Workup

  1. waitleft
  2. filtrationThe suspension was filtered
  3. washwashing with ethyl acetate
  4. customto give a solid which
  5. customwas recrystallized from methanol/water/isopropanol (final volume 50 mL)

Sources & evidence

ORD record
ord-589f6b9d6c3c4c1daab3f3798ec7db52
Source dataset
uspto-grants-1993_08
Patent number
US05240946

Reaction notes

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