HCID 22499792, compound → HCID 10215048, compound

HRID 1815117Notes

Reaction equation

HRID 1815117 reaction equation
[CH:1]1([C:6]([OH:27])([C:17]#[C:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:7][C:8]2[O:13]C(C)(C)O[C:10](=[O:16])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CO>[CH:1]1([C:6]2([C:17]#[C:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[O:27][C:10](=[O:16])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 1

HCID 22499792HCID 22499792, compound

Product 1

HCID 10215048HCID 10215048, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-[2-cyclopentyl-2-hydroxy-4-(4-methoxy-phenyl)-but-3-ynyl]-2,2-dimethyl-[1,3]dioxin-4-one (55 mg, 0.1485 mmol), 1NaOH n(150 μL, 0.1485 mmol), and MeOH (1.5 mL), was stirred at room temperature for 2 hours, at which time HPLC indicated that all starting material had been consumed. The reaction was quenched with 0.5 N citric acid, and extracted with ethylacetate. The organic layer was dried with MgSO4, concentrated and purified by preparative HPLC, giving 13 mg of the product (24% yield). 1H NMR (CDCl3): δ 1.73 (m, 4H), 2.23 (pentet, 1H, J=8.1 Hz), 2.85 (d, 1H, J=16.3 Hz), 2.95 (d, 1H, J=16.5 Hz), 3.45 (d, 1H, J=21.5 Hz), 3.85 (s, 3H), 3.98 (d, 1H, J=22.0 Hz), 6.84 (d, 2H, J=8.7 Hz), 7.32 (d, 2H, J=8.1 Hz); ESIMS (M+Na+): 335.1.

Workup

  1. customhad been consumed
  2. customThe reaction was quenched with 0.5 N citric acid
  3. extractionextracted with ethylacetate
  4. dry with materialThe organic layer was dried with MgSO4
  5. concentrationconcentrated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-3c20ac2c9c2b4f98a7ee57c15556950f
Source dataset
uspto-grants-2005_04
Patent number
US06878727B2

Reaction notes

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