Tetrahydrofuran → HCID 66660576, compound

HRID 2391054Notes

Reaction equation

HRID 2391054 reaction equation
[CH:1]([O:4][C:5]([C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:26][N:25]=[C:24]([CH3:27])[C:23]=4[C:28]([O:30]C)=[O:29])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])C.[OH-].[Na+].[CH2:34]1COCC1>C(O)C.O>[CH2:1]([O:4][C:5]([C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:26][N:25]=[C:24]([CH3:27])[C:23]=4[C:28]([OH:30])=[O:29])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)=[O:6])[CH2:3][CH3:34]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66660628HCID 66660628, compound

Product 1

HCID 66660576HCID 66660576, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To the methyl ester from Step 5 (5.2 g, 12.4 mmol) in THF (100 mL) and ethanol (20 mL) was added a solution of sodium hydroxide (1.5 g, 37.2 mmol) in water (40 mL). The solution was stirred at room temperature 3 hours. ˜50 mL solvent evaporated and 200 mL water added. The product was precipitated out of solution with dilute hydrochloric acid to pH 2. The product was isolated by filtration to yield 4.6 grams of the title compound.

Workup

  1. custom˜50 mL solvent evaporated
  2. addition200 mL water added
  3. customThe product was precipitated out of solution with dilute hydrochloric acid to pH 2
  4. customThe product was isolated by filtration

Sources & evidence

ORD record
ord-de964607ba2749299f33031217b19963
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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