Water → HCID 11347841, compound

HRID 1394004Notes

Reaction equation

HRID 1394004 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].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

4

Reactant 2

HCID 962WaterHCID 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-2103413a9210487fa45f9ce7fa4bea4e
Source dataset
uspto-grants-2008_03
Patent number
US07348310B2

Reaction notes

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