Sodium Hydroxide → HCID 46836306, compound

HRID 1518335Notes

Reaction equation

HRID 1518335 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:33][CH2:34][O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:26]([C:28]([O:30]CC)=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].[OH-].[Na+]>C1COCC1.CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:33][CH2:34][O:35][CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59447515HCID 59447515, compound

Product 1

HCID 46836306HCID 46836306, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To compound 55A (138 mg, 0.230 mmol) in THF (3 ml) and MeOH (3 ml) was treated with 10% sodium hydroxide (0.46 ml, 1.152 mmol) for 1 day. The reaction mixture was concentrated and acidified by conc. HCl. The precipitate was collected by filtration and dried to provide the title compound: 1H NMR (500 MHz, DMSO-D6) δ ppm 12.89 (2H, s), 8.03 (1H, d), 7.80 (1H, d), 7.67 (1H, d), 7.42-7.51 (2H, m), 7.33-7.42 (2H, m), 7.25-7.31 (4H, m), 7.17-7.21 (1H, m), 4.82 (2H, s), 4.46 (2H, s), 3.74 (2H, t), 3.60 (2H, t), 3.28-3.35 (2H, m), 3.03 (2H, t); LCMS (APCI) m/e 571.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationThe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-293b644059dd4069a9476ffe3a5ef432
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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