HCID 10805016, compound → HCID 10300386, compound

HRID 1282300Notes

Reaction equation

HRID 1282300 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:9]([C:15](Cl)=[O:16])=[C:8]([CH3:18])[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]=2[N:4]=1.Cl.[NH2:23][C@H:24]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:9]([C:15]([NH:23][C@@H:24]([CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])=[O:16])=[C:8]([CH3:18])[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 10805016HCID 10805016, compoundHCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)

Product 1

HCID 10300386HCID 10300386, compound

Procedure

Prepared from 2,3-dimethoxy-6-methyl-7-nitro-quinoxaline-5-carbonyl chloride (13) 200 mg (0.64 mmol) and L-phenylalanine, tert-butyl ester hydrochloride 173 mg (0.67 mmol). Reaction was continued for 24 hours, and the crude product was eluted through a flash column (4:1 hexanes:ethyl acetate), 180 mg (57%), mp 86-88° C.; 1H NMR (CDCl3): δ 8.32 (s, 1H), 7.22 (m, 5H), 6.39 (d, 1H, J=6.6 Hz), 4.88 (q, 1H, J=6.1, J=6.8 Hz), 4.07 (s, 3H), 4.00 (s, 3H), 3.23 (d, 2H, J=5.9 Hz), 2.56 (s, 3H), 1.37 (s, 9H); MS (APCI): m/z 497 (M+H). Anal. Calcd. for C25H28N4O7: C, 60.48; H, 5.68; N, 11.28. Found: C, 59.73; H, 5.53; N, 11.28.

Workup

  1. customReaction
  2. washthe crude product was eluted through a flash column (4:1 hexanes:ethyl acetate), 180 mg (57%), mp 86-88° C.

Sources & evidence

ORD record
ord-e731c8fe28d1466a9c2517bbe7f92b79
Source dataset
uspto-grants-2002_09
Patent number
US06455698B1

Reaction notes

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