Sodium Hydroxide → HCID 118060045, compound

HRID 920819Notes

Reaction equation

HRID 920819 reaction equation
C([C:3]1([C:21]([O-:23])=[O:22])[CH:7]2[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:10]([CH3:12])[CH2:11][N:6]2[N:5]=[C:4]1[I:20])C.[OH-].[Na+]>CCO.O>[C:16]([O:15][C:13]([N:9]1[CH:10]([CH3:12])[CH2:11][N:6]2[N:5]=[C:4]([I:20])[C:3]([C:21]([OH:23])=[O:22])=[C:7]2[CH2:8]1)=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 131734890HCID 131734890, compound

Product 1

HCID 118060045HCID 118060045, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of Intermediate 340D (0.85 g, 1.953 mmol) in EtOH (2.0 mL) was added a solution of NaOH (0.391 g, 9.76 mmol) in water (1.0 mL) and the resulting solution was stirred at RT for 16 h. The reaction mixture was concentrated and the residue was acidified by the addition of a 1N aq. solution of HCl (5 mL) which was allowed to stir for 10 min. The generated precipitate was filtered and dried to afford Intermediate 340E as a white solid (0.65 g, 82%). MS(ES): m/z=408 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 5.05 (d, J=18.89 Hz, 1H), 4.67 (br. s., 1H), 4.36 (d, J=18.13 Hz, 1H), 4.13-4.25 (m, 1H), 3.93-4.13 (m, 2H), 1.44 (s, 9H), 1.08 (t, J=6.99 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was acidified by the addition of a 1N aq. solution of HCl (5 mL) which
  3. stirringto stir for 10 min
  4. filtrationThe generated precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-d85aaf71cd374067afcfa2e258240001
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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