Water → HCID 131736596, compound

HRID 1479849Notes

Reaction equation

HRID 1479849 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:19][CH3:20])[C:12]2([C:15]([O:17]C)=[O:16])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.O[Li].O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:19][CH3:20])[C:12]2([C:15]([OH:17])=[O:16])[CH2:14][CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 131736595HCID 131736595, compound

Product 1

HCID 131736596HCID 131736596, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 14B (750 mg, 2.36 mmol) dissolved in THF (10 ml) and water (5 ml) was added with LiOH.H2O (3 equiv., 297 mg) and the reaction was stirred at rt 3 hours. The reaction was concentrated under vacuum. Water was added and 10% HCl till precipitation of the acid. The acid was extracted with ethyl acetate and the organic phase was washed with Brine, dried over sodium sulfate and concentrated under vacuum to give 650 mg of 15B as a white solid. Yield=90%. 1HNMR (DMSO, 200 MHz) δ 1.06 (3H, t, J=7.2 Hz), 1.38 (2H, m), 1.35 (2H, bs), 3.33 (2H, m), 7.43 (2H, m), 7.77 (2H, m), 12.46 (1H, bs)

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. additionWater was added
  3. custom10% HCl till precipitation of the acid
  4. extractionThe acid was extracted with ethyl acetate
  5. washthe organic phase was washed with Brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c4d0330455f944578b772dcf4bd40f27
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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