Sodium Hydroxide → HCID 49783010, compound

HRID 929503Notes

Reaction equation

HRID 929503 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:24])[NH:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=2)[CH2:7][CH2:6]1)(=[O:4])[CH2:2][CH3:3].[OH-].[Na+]>C(O)C>[C:1]([N:5]1[CH2:6][CH2:7][CH:8]([NH:11][C:12](=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:22][CH:23]=2)[CH2:9][CH2:10]1)(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 49783009HCID 49783009, compound

Product 1

HCID 49783010HCID 49783010, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 21 (85 mg, 0.25 mmol) was refluxed in ethanol (10 mL) containing 1M NaOH (300 μl, 1.2 eq) for 5 hours. Additional base (300 μl) was added and the reaction continued for 2 hours before cooling to RT The reaction was quenched with 1N HCl (20 mL), the organic solvent removed and the remaining suspension filtered to give compound 22 (49 mg, 60%) as a white solid: MP 201-204° C. 1H NMR (500 MHz, DMSO-d6) δ 12.50 (s, 1H), 8.73 (s, 1H), 7.80 (d, J=8.7 Hz, 2H), 7.47 (d, J=8.7 Hz, 2H), 6.32 (d, J=7.6 Hz, 1H), 3.13 (t, J=12.1 Hz, 1H), 2.80 (t, J=11.8 Hz, 1H), 2.32 (q, J=7.4 Hz, 2H), 0.98 (t, J=7.4 Hz, 3H). Purity 94%. HRMS calculated for C16H21N3O4−H+ 318.1454. found (ESI(−), [M−H]) 318.1498.

Workup

  1. customwas quenched with 1N HCl (20 mL)
  2. customthe organic solvent removed
  3. filtrationthe remaining suspension filtered

Sources & evidence

ORD record
ord-d79a8b155014445bb7983a54a6f7348a
Source dataset
uspto-grants-2016_03
Patent number
US09296693B2

Reaction notes

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