Sodium Hydroxide → HCID 22730320, compound

HRID 2085709Notes

Reaction equation

HRID 2085709 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-d4a0e54ddd4a4ac58f74d6ebd4dd541e
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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