Tetrahydrofuran → N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-oxalamic acid

HRID 2235812Notes

Reaction equation

HRID 2235812 reaction equation
C[O:2][C:3](=[O:29])[C:4]([NH:6][C:7]1[C:12]2[N:13]([CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)[C:14](=[O:17])[CH2:15][O:16][C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:5].[OH-].[Na+].C1COCC1>CO>[CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[CH2:18][N:13]1[C:12]2[C:7]([NH:6][C:4](=[O:5])[C:3]([OH:29])=[O:2])=[CH:8][CH:9]=[CH:10][C:11]=2[O:16][CH2:15][C:14]1=[O:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66917760N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-oxalamic acid methyl ester

Product 1

HCID 66917711N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-oxalamic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-oxalamic acid methyl ester, K-67 (95 mg,) in methanol (2.0 mL), 1.0 M NaOH (0.5 mL) was added followed by THF (2.0 mL) resulting in a clear solution. Reaction was stirred at room temperature for 30 minutes and then concentrated to remove the solvents. The residue was taken in water (2.0 mL), acidified with 1.0 M HCl and extracted with ethyl acetate (5.0 mL×4). Combined extracts were washed with water (5.0 mL), dried (brine, Na2SO4) and concentrated to afford N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo [1,4]oxazin-5-yl)-oxalamic acid, A51 (69 mg). 1H NMR (CDCl3) 4.66 (s, 2H), 5.21 (s, 2H), 7.02 (m, 2H), 7.07 (d, J=8.5 Hz, 1H), 7.14 (br s, 1H), 7.33 (br s, 2H), 7.50 (s, 1H), 7.65 (m, 3H), 8.69 (s, 1H). MS (ESI−) Calcd. for: 376.4; Found: 375.5 (M−H).

Workup

  1. customresulting in a clear solution
  2. customReaction
  3. concentrationconcentrated
  4. customto remove the solvents
  5. extractionextracted with ethyl acetate (5.0 mL×4)
  6. washCombined extracts were washed with water (5.0 mL)
  7. dry with materialdried (brine, Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-03b4da4b30134175bc929f01317f2003
Source dataset
uspto-grants-2010_05
Patent number
US07714017B2

Reaction notes

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