Sodium Hydroxide → HCID 117642466, compound

HRID 588757Notes

Reaction equation

HRID 588757 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[O:23])[CH2:18][CH2:17]2)[C:5]2[C:10]([C:11]([O:13]CC)=[O:12])=[CH:9][S:8][C:6]=2[N:7]=1.[OH-].[Na+]>C(O)C.C1COCC1>[NH2:1][C:2]1[N:3]=[C:4]([N:16]2[CH2:17][CH2:18][N:19]([C:22](=[O:23])[NH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[CH2:20][CH2:21]2)[C:5]2[C:10]([C:11]([OH:13])=[O:12])=[CH:9][S:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117642729HCID 117642729, compound

Product 1

HCID 117642466HCID 117642466, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Example 21 (900 mg, 1.97 mmol) in ethanol/THF (1:1, 10 mL) was added aqueous NaOH solution (2M, 10 mL). The reaction mixture was heated to 50° C. for 12 hours. On completion, the reaction mixture was concentrated in vacuo and then re-dissolved in warm water. The pH was adjusted to pH 5-6 with 2M HCl, and the precipitate was filtered and dried on a sinter to give the title compound (460 mg) as a white solid. δH (DMSO-d6, 300 MHz) 8.43 (1H, s), 7.68 (1H, s), 7.35 (2H, d, J 8.8 Hz), 6.82 (2H, d, J 8.8 Hz), 6.44 (2H, br s), 3.70 (3H, s), 3.49-3.34 (8H, br m+H2O). LCMS (pH 10) MH+ 429, RT 0.79 minutes. LCMS (pH 3) MH+ 429, RT 1.15 minutes.

Workup

  1. concentrationOn completion, the reaction mixture was concentrated in vacuo
  2. dissolutionre-dissolved in warm water
  3. filtrationthe precipitate was filtered
  4. customdried on a sinter

Sources & evidence

ORD record
ord-a8812371c51e47beb0218d1a35eb7788
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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