Glycine → HCID 19063687, compound

HRID 482348Notes

Reaction equation

HRID 482348 reaction equation
O=[C:2]1[N:7]([CH2:8][C:9]([N:11]([CH:18]([CH3:20])[CH3:19])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[C:6]2[CH:21]=[CH:22][CH2:23][CH2:24][C:5]=2[C:4](=[O:25])[O:3]1.[NH2:26][CH2:27]C(O)=O.C(N(CC)CC)C>O>[O:3]=[C:2]1[N:7]([CH2:8][C:9]([N:11]([CH:18]([CH3:20])[CH3:19])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])[C:6]2[CH:21]=[CH:22][CH:23]=[CH:24][C:5]=2[C:4](=[O:25])[NH:26][CH2:27]1

Participants

5

Reactant 3

HCID 750GlycineHCID 8471TriethylamineHCID 86753035HCID 86753035, compound

Product 1

HCID 19063687HCID 19063687, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 2-(2,4-dioxo-6H-benzo[d][1,3]oxazin-1-yl)-N-isopropyl-N-phenylacetamide (10 g, 31 mmol), glycine (2.32 g, 31 mmol) and triethylamine (4.32 mL, 31 mmol) in water (50 mL) is stirred at 50° C. for 5 h. The reaction mixture is concentrated to a brown viscous oil, acetic acid (100 mL) is added and the mixture heated at reflux for 6 h. The reaction mixture is concentrated to a brown viscous oil, dissolved in ethyl acetate (300 mL) and washed with water, saturated aqueous sodium bicarbonate and brine. The resulting solution is dried over magnesium sulfate and concentrated to a yellow foam. Recrystallization from ethyl acetate/petroleum ether (4:1, 100 mL) gave the title compound (7.55 g, 21.5 mmol) as an off-white powder. 1H NMR (300M Hz, CDCl3): 1.12 (d, J=6.7 Hz, 6H); 3.6-6.4 (m, 4H); 5.05 (m, J=6.7 Hz, 1H); 6.62 (m, 1H); 7.1-7.6 (m, 7H); 7.84 (d, J=7.5 Hz, 1H). MS (FAB): [M+H]+ =352.

Workup

  1. concentrationThe reaction mixture is concentrated to a brown viscous oil, acetic acid (100 mL)
  2. additionis added
  3. temperaturethe mixture heated
  4. temperatureat reflux for 6 h
  5. concentrationThe reaction mixture is concentrated to a brown viscous oil
  6. dissolutiondissolved in ethyl acetate (300 mL)
  7. washwashed with water, saturated aqueous sodium bicarbonate and brine
  8. dry with materialThe resulting solution is dried over magnesium sulfate
  9. concentrationconcentrated to a yellow foam
  10. customRecrystallization from ethyl acetate/petroleum ether (4:1, 100 mL)

Sources & evidence

ORD record
ord-d5241cee070a44d0a41fff0742501aa4
Source dataset
uspto-grants-1998_08
Patent number
US05795887

Reaction notes

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