Sodium Hydroxide → HCID 58134829, compound

HRID 1396090Notes

Reaction equation

HRID 1396090 reaction equation
[NH2:1][C:2]1[C:17]2[C:16](=[O:18])[C:15]([C:19]([O:21]CC)=[O:20])=[CH:14][N:7]3[CH2:8][C:9]4([CH2:13][CH2:12][CH2:11]4)[O:10][C:5]([C:6]=23)=[C:4]([F:24])[C:3]=1[F:25].[OH-].[Na+]>CCO>[NH2:1][C:2]1[C:17]2[C:16](=[O:18])[C:15]([C:19]([OH:21])=[O:20])=[CH:14][N:7]3[CH2:8][C:9]4([CH2:13][CH2:12][CH2:11]4)[O:10][C:5]([C:6]=23)=[C:4]([F:24])[C:3]=1[F:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58134838HCID 58134838, compound

Product 1

HCID 58134829HCID 58134829, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 8′-amino-9′,10′-difluoro-7′-oxospiro[cyclobutane-1,2′(3′H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6′-carboxylate (247 mg, 0.705 mmol) and 1M NaOH aq. (3.5 mL) in EtOH (3.5 mL) was stirred at room 50° C. for 1.5 hours. The solvent was removed and the residue was dissolved in water. The solution was acidified to pH 7 with 2M HCl and the resulting precipitate was removed by filtration, washed with water and dried to yield the title compound (216 mg, 95%) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 1.73-1.97 (2H, m), 2.04-2.27 (4H, m), 4.50 (2H, s), 7.25 (2H, brs), 8.76 (1H, s), 14.67 (1H, s). ESIMS (+): 322[M+H]+.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in water
  3. customthe resulting precipitate was removed by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8aeb8cb275794dfd8dea0aeb2df861c8
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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