Sodium Hydroxide → HCID 22730320, compound

HRID 2356041Notes

Reaction equation

HRID 2356041 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[O:19])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>C1COCC1.CO>[CH2:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][N:12]([C:9]2[CH:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:11][CH:10]=2)[CH2:13][CH2:14]1)=[O:19])[CH:22]([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22730547HCID 22730547, compound

Product 1

HCID 22730320HCID 22730320, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of Example 131B (2.8 g, 8.37 mmol) and 4M aqueous NaOH (10 mL) in 1:1 THF/methanol (40 mL) was heated to reflux for 18 hours, and concentrated. The concentrate was diluted with water and adjusted to pH 1 with concentrated HCl, treated with isobutyl chloroformate (3 mL), slowly adjusted to pH 12 with NaOH, and adjusted to pH 2 with HCl. The mixture was filtered and the filter cake was dried under vacuum to provide the desired product. MS (ESI(−)) m/e 305 (M−H)−.

Workup

  1. temperatureto reflux for 18 hours
  2. concentrationconcentrated
  3. additionThe concentrate was diluted with water
  4. additiontreated with isobutyl chloroformate (3 mL)
  5. filtrationThe mixture was filtered
  6. customthe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-076418ca9ec34ff1bf45f24be362a779
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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