Water → HCID 11347841, compound

HRID 2243836Notes

Reaction equation

HRID 2243836 reaction equation
[CH3:1][C:2](=[CH2:30])[C:3]([N:5]1[C@@:9]2([CH2:13][CH2:12][N:11]([C@@H:14]([C:19]([O:21]CC3C=CC=CC=3)=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]2=[O:29])[CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].O>CO>[CH3:30][C:2](=[CH2:1])[C:3]([N:5]1[C@@:9]2([CH2:13][CH2:12][N:11]([C@@H:14]([C:19]([OH:21])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]2=[O:29])[CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11223672HCID 11223672, compound

Product 1

HCID 11347841HCID 11347841, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 15 (65 mg, 0.16 mmol) in methanol (2.5 ml) were added aq. NaOH (1.6 ml, 1N) and H2O (1.6 ml) and the mixture was stirred at room temperature for 1 h. The resulting mixture was concentrated at reduced pressure, and the residue was partitioned between H2O (20 ml) and DCM (20 ml). The aqueous phase was acidified to pH=2 with aq HCl (10 ml, 0.1 N) and extracted with DCM (3×20 ml). The combined organic phases were washed with brine (25 ml), dried (Na2SO4) and concentrated at reduced pressure to afford 18 (44 mg, 85%) as a white solid. HPLC [Column Novapack C18 (Waters), 3.9×150 mm, Φ=1 ml/min, λ=214 nm, eluent: ACN/0.05% TFA, (25/75)] Rt=6.38 min.

Workup

  1. concentrationThe resulting mixture was concentrated at reduced pressure
  2. customthe residue was partitioned between H2O (20 ml) and DCM (20 ml)
  3. extractionextracted with DCM (3×20 ml)
  4. washThe combined organic phases were washed with brine (25 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-46f72b7dcde74297807404dd3765b592
Source dataset
uspto-grants-2010_03
Patent number
US07678765B2

Reaction notes

Loading…