Water → 2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-ylcarbonyl)aminobenzoic Acid

HRID 1882989Notes

Reaction equation

HRID 1882989 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]([O:18]C)=[O:17])=[O:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[OH-].[Na+].CCOC(C)=O.O>O1CCOCC1>[O:4]1[C:5]2([CH2:6][CH2:7][N:8]([C:11]([NH:13][C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]([OH:18])=[O:17])=[O:12])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 17383362Methyl 2-[(1,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)amino]benzoate

Product 1

HCID 219062722-(1,4-Dioxa-8-azaspiro[4.5]decan-8-ylcarbonyl)aminobenzoic Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 2-(1,4-dioxa-8-azaspiro(4.5]decan-8-ylcarbonyl)aminobenzoate (2.00 g, 6.25 mmol) in dioxane (30 mL) was treated with 5 N NaOH (12.5 mL). After 1 h, the mixture was poured into EtOAc and water, and the aqueous layer was washed with EtOAc. The pH of the aqueous layer was then adjusted to 2-3 by addition of 5 N HCl and washed with EtOAc (3×) The combined organic layers were washed with brine, dried with sodium sulfate, and concentrated, yielding the title compound; which was used without further purification.

Workup

  1. washthe aqueous layer was washed with EtOAc
  2. additionThe pH of the aqueous layer was then adjusted to 2-3 by addition of 5 N HCl
  3. washwashed with EtOAc (3×) The combined organic layers
  4. washwere washed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-af157a5e3bf341e89b7927c44c417f88
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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