Sodium Hydroxide → HCID 58762516, compound

HRID 1453316Notes

Reaction equation

HRID 1453316 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][C:5](=[O:27])[CH2:6][C:7]([CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)(O)[CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([OH:19])=[CH:14][C:13]=1[CH3:20].[OH-].[Na+]>>[CH:22]1([C:7]2([CH2:8][CH2:9][C:10]#[C:11][C:12]3[CH:17]=[C:16]([CH3:18])[C:15]([OH:19])=[CH:14][C:13]=3[CH3:20])[O:28][C:3](=[O:2])[CH2:4][C:5](=[O:27])[CH2:6]2)[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 587623975-Cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic Acid Methyl Ester

Product 1

HCID 58762516HCID 58762516, compoundYield 98.3%

Procedure

To 5-cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic acid methyl ester (60 mg, 0.155 mmol) from Step 2 below was added NaOH (0.3 M in MeOH, 1 mL, 0.31 mmol). The solution was stirred overnight, and then quenched with 1 N HCl (5 mL). The solution was extracted with 4×10 mL CH2Cl2. The organic layer was dried over Na2SO4, and then the solids were removed by filtration. After concentrating the mother liquor, the resulting oil was purified by flash chromatography to yield the desired product (54 mg, 98% yield). 1H NMR (CDCl3) δ: 1.35-1.75 (m, 8H), 1.93-1.99 (m, 3H), 2.10 (s, 3H), 2.23 (s, 3H), 2.51 (t, J=7.33 Hz, 2H), 2.69 (d, J=16.17 Hz, 1H), 2.83 (d, J=16.18 Hz, 1H), 3.37 (s, 2H), 4.66 (s, 1H), 6.52 (s, 1H), 7.05 (s, 1H). MS (ESI): 353 (M−H).

Workup

  1. customquenched with 1 N HCl (5 mL)
  2. extractionThe solution was extracted with 4×10 mL CH2Cl2
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solids were removed by filtration
  5. concentrationAfter concentrating the mother liquor
  6. customthe resulting oil was purified by flash chromatography

Sources & evidence

ORD record
ord-d6109f9b47324adbb7d7f892aec551eb
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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