Water → HCID 70913731, compound

HRID 1844751Notes

Reaction equation

HRID 1844751 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:20]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:19]([CH3:28])=[C:18]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:17]=2)[CH:8]=[C:9]([C:11]([C:14]#N)([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:33].[Na+].[OH2:35]>CCO>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:12])([CH3:13])[C:14]([OH:35])=[O:33])[CH:8]=[C:7]([C:16]2[N:20]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:19]([CH3:28])=[C:18]([S:29](=[O:31])(=[O:30])[NH2:32])[CH:17]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66562431HCID 66562431, compound

Product 1

HCID 70913731HCID 70913731, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound 45 (720 mg, 1.58 mmol) and NaOH (5.0 g, 127 mmol) in a mixture of EtOH (15 mL) and H2O (10 mL) was stirred at reflux for 3 d, cooled to rt, concentrated and redissolved in H2O (30 mL) and acidified with 1N HCl solution to pH=6. The formed solid was collected by filtration, washed with EA and dried in vacuum to give the title compound 46 (750 mg, 100%) as a white solid. 1H-NMR (DMSO-d6, 400 MHz) δ: 0.63-0.65 (2H, m), 0.90-0.95 (3H, m), 1.22-1.25 (3H, m), 1.30 (9H, s), 1.45 (3H, m), 1.49 (6H, s), 2.43 (3H, s), 3.76 (2H, d, J=6.8 Hz), 6.29 (1H, s), 6.92 (2H, s), 7.08 (1H, s), 7.23 (1H, s), 7.34 (1H, s), 12.38 (1H, s). MS Calcd.: 474; MS Found: 475 (M+1).

Workup

  1. temperatureat reflux for 3 d
  2. concentrationconcentrated
  3. dissolutionredissolved in H2O (30 mL)
  4. filtrationThe formed solid was collected by filtration
  5. washwashed with EA
  6. customdried in vacuum

Sources & evidence

ORD record
ord-492a32a0ca7d454497a5f1e9894bc70f
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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