Sodium Hydroxide → HCID 118208611, compound

HRID 595201Notes

Reaction equation

HRID 595201 reaction equation
[OH-].[Na+].[N+](C1C=CC(C([O:12][CH2:13][C@:14]([OH:23])([CH3:22])[CH2:15][N:16]2[CH:20]=[C:19]([I:21])[CH:18]=[N:17]2)=O)=CC=1)([O-])=O>C(#N)C>[I:21][C:19]1[CH:18]=[N:17][N:16]([CH2:15][C@:14]([CH3:22])([OH:23])[CH2:13][OH:12])[CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118208680HCID 118208680, compound

Product 1

HCID 118208611HCID 118208611, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium hydroxide (3 M in water, 3.25 mL, 9.74 mmol) was added to a solution of (S)-2-hydroxy-3-(4-iodo-1H-pyrazol-1-yl)-2-methylpropyl 4-nitrobenzoate (2.80 g, 6.49 mmol) in acetonitrile (40 mL). The mixture was stirred at room temperature for 1 h, then concentrated under reduced pressure, diluted with EtOAc, and washed with hydrochloric acid (1N), water and brine. The organic layers were separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-10% MeOH/DCM) to afford (S)-3-(4-iodo-1H-pyrazol-1-yl)-2-methylpropane-1,2-diol. MS ESI calc'd. for C17H12N2O2 [M+H]+ 283. found 283. 1H NMR (500 MHz, DMSO-d6) δ 7.76 (s, 1H), 7.48 (s, 1H), 4.79 (t, J=5.5 Hz, 1H), 4.53 (s, 1H), 4.09-4.00 (m, 2H), 3.17-3.11 (m, 2H), 0.89 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washwashed with hydrochloric acid (1N), water and brine
  4. customThe organic layers were separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-522c58b48bb0449c904bf87ab8d5f13e
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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