Sodium Hydroxide → HCID 58168164, compound

HRID 1029266Notes

Reaction equation

HRID 1029266 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][C:20]=3[NH:22][C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:37])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:25][CH:24]=3)[NH:15][C:14](=[O:38])[C:13]=12)=[O:7])C>C1COCC1>[C:30]([NH:29][C:26]1[CH:25]=[CH:24][C:23]([NH:22][C:20]2[CH:19]=[CH:18][N:17]=[C:16]3[C:21]=2[C:12]2[C:13](=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[CH:10][CH:11]=2)[C:14](=[O:38])[NH:15]3)=[CH:28][CH:27]=1)(=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44208224HCID 44208224, compound

Product 1

HCID 58168164HCID 58168164, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaOH (4.2 mL, 1.00 M, 4.18 mmol) was added to a suspension of 423 (200 mg, 0.42 mmol) in THF (5 mL), and stirred overnight at room temperature. The crude reaction mixture was purified directly via HP-LC to provide 434 (17 mg) as a solid. LC-MS (M+H=451, obsd.=451). 1H NMR (400 MHz, DMSO-d6): δ 6.93 (d, 1H), 7.20 (d, 2H), 7.54 (m, 3H), 7.76 (m, 2H), 7.78 (d, 1H), 7.97 (d, 1H), 8.10 (d, 1H), 8.27 (s, 1H), 8.85 (d, 1H), 9.18 (s, 1H), 10.27 (s, 1H).

Workup

  1. customThe crude reaction mixture
  2. customwas purified directly via HP-LC

Sources & evidence

ORD record
ord-34bbd3451cf748f9aa10c6739efa4656
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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