Triethylamine → HCID 131720802, compound

HRID 482356Notes

Reaction equation

HRID 482356 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9]([N:11]([CH:20]([CH3:22])[CH3:21])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[O:10])[C:6]2[CH:23]=[CH:24][CH2:25][CH2:26][C:5]=2[C:4](=O)[O:3]1.[NH2:28][C@@H:29](C(O)=O)[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1.C(N(CC)CC)C>O>[NH:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:31]([CH2:30][C@@H:29]2[C:2](=[O:1])[N:7]([CH2:8][C:9]([N:11]([CH:20]([CH3:22])[CH3:21])[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[O:10])[C:6]3[CH:23]=[CH:24][CH:25]=[CH:26][C:5]=3[C:4](=[O:3])[NH:28]2)=[CH:32]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9060D-TryptophanHCID 131720803HCID 131720803, compound

Product 1

HCID 131720802HCID 131720802, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2,4-Dioxo-6H-benzo[d][1,3]oxazin-1-yl)-N-isopropyl-N-(4-methyoxy-phenyl)-acetamide (1.00 g, 2.71 mmol), D-tryptophan (554 mg, 2.71 mmol) and triethylamine (0.378 mL, 2.71 mmol) are combined in water (20 mL) and stirred for 5 hrs. at 50° C. After concentration in vacuo, the reaction mixture is combined with glacial acetic acid (20 mL) and refluxed for 5 hrs. The reaction mixture is filtered and then concentrated in vacuo to an oil. The oil is dissolved in ethyl acetate and washed consecutively with water (2×), saturated aqueous sodium bicarbonate, and brine. The solution is dried over anyhydrous magnesium sulfate, filtered, treated with activated charcoal, filtered and concentrated in vacuo to a yellow foam. The product is crystallized from methanol (15 mL). The resulting slurry is cooled with an ice/water bath, filtered and washed with cold methanol (3×4 mL), and dried under high vacuum to provide the title compound as white solid (469 mg, 0.918 mmol). 1H NMR (300 MHz, CDCl3): 1.11 (m, 6H); 3.22 (m, 1H); 3.46 (m, 1H); 3.69 (d, 1H, J=16.6 Hz); 3.83 (s, 3H); 4.20 (m, 1H); 4.45 (d, 1H, J=16.6 Hz); 5.06 (m, 1H); 6.06 (d, 1H, J=5.4 Hz); 6.88-7.37 (m, 10H); 7.50 (m, 2H); 7.73 (m, 1H); 8.14 (s, 1H). MS(FAB): [M+H]+ =511.

Workup

  1. customat 50° C
  2. concentrationAfter concentration in vacuo
  3. temperaturerefluxed for 5 hrs
  4. filtrationThe reaction mixture is filtered
  5. concentrationconcentrated in vacuo to an oil
  6. dissolutionThe oil is dissolved in ethyl acetate
  7. washwashed consecutively with water (2×), saturated aqueous sodium bicarbonate, and brine
  8. dry with materialThe solution is dried over anyhydrous magnesium sulfate
  9. filtrationfiltered
  10. additiontreated with activated charcoal
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo to a yellow foam
  13. customThe product is crystallized from methanol (15 mL)
  14. temperatureThe resulting slurry is cooled with an ice/water bath
  15. filtrationfiltered
  16. washwashed with cold methanol (3×4 mL)
  17. customdried under high vacuum

Sources & evidence

ORD record
ord-da28839dd0f3474080adfe4273d800df
Source dataset
uspto-grants-1998_08
Patent number
US05795887

Reaction notes

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