Methanol → HCID 16731515, compound

HRID 501658Notes

Reaction equation

HRID 501658 reaction equation
C([O:9][C@H:10]1[C@@H:17]2[N:13]([C:14](=[O:30])[N:15]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([Cl:28])[C:21]=3[CH3:29])[C@H:16]2[CH2:18][CH3:19])[CH2:12][CH2:11]1)(=O)C1C=CC=CC=1.[OH-].[K+].CO>C1COCC1.CCOC(C)=O>[CH2:18]([C@@H:16]1[N:15]([C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([Cl:28])[C:21]=2[CH3:29])[C:14](=[O:30])[N:13]2[CH2:12][CH2:11][C@@H:10]([OH:9])[C@@H:17]12)[CH3:19]

Participants

6

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 16731513HCID 16731513, compound

Product 1

HCID 16731515HCID 16731515, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 87A (64 mg, 0.15 mmol) was dissolved in 1.5 mL of THF, treated with 1N KOH in anhydrous methanol (0.32 mL, 0.32 mmol) at rt for 2 h. Diluted the reaction mixture with 30 mL EtOAc, washed with saturated aqueous NaHCO3 solution (10 mL), brine (10 mL×2), dried over MgSO4, filtered and concentrated. The resulting mixture was purified by reverse phase HPLC (Phenomenex Luna 30×250 mm S5 C18, 30 min. gradient time, 25 mL/min, 30-100% B solvent, A=10% MeOH/water, B=90% MeOH/Water), provided the title compound (43 mg). Analytical HPLC retention time 2.947 min (purity 98%). Condition: YMC Combiscreen ODS-A C18 4.6×50 mm column, 4 min gradient, 4 mL/min flow, 0-100% B solvent, A=10% MeOH/water+0.1% H3PO4, B=90% MeOH/Water+0.1% H3PO4. MS (ES) m/z 320.24 [M+H]+, HRMS calcd for [M+H] 320.1166, found 320.1152.

Workup

  1. washwashed with saturated aqueous NaHCO3 solution (10 mL), brine (10 mL×2)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting mixture was purified by reverse phase HPLC (Phenomenex Luna 30×250 mm S5 C18, 30 min. gradient time, 25 mL/min, 30-100% B solvent

Sources & evidence

ORD record
ord-e23f0f71cd3746b4abeabcb61bab21de
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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