Lithium hydroxide, monohydrate → HCID 23579171, compound

HRID 1827333Notes

Reaction equation

HRID 1827333 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH:13]=[CH:14]/[C:15]([O:17]CC)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O>CCO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 23579175HCID 23579175, compound

Product 1

HCID 23579171HCID 23579171, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the above ethyl ester (15) (140 mg, 0.52 mmol) in absolute EtOH (4 mL) was added LiOH—H2O (0.75 mL, 1.5 mmol, 2N solution in water). The reaction was heated at 50° C. for 1 h, then concentrated to remove excess EtOH. After acidification with 5% citric acid (20 mL), the product was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4) and concentrated to give a white solid (16) (110 mg, 88%). 1H NMR (400 MHz, CDCL3) δ 7.31 (dd, J=15.2, 10.8 Hz, 1H), 6.25 (dd, J=15.2, 10.8 Hz, 1H), 6.11 (quintet, J=7.2 Hz, 1H), 5.81 (d, J=15.2 Hz, 1H), 4.58 (br s, 1H), 3.24 (m, 2H), 2.37 (m, 2H), 1.44 (s, 9H); MS (ESI−) m/z 240.11 (M−H+).

Workup

  1. concentrationconcentrated
  2. customto remove excess EtOH
  3. extractionAfter acidification with 5% citric acid (20 mL), the product was extracted with EtOAc (2×50 mL)
  4. washThe combined organic extracts were washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-da244724b3c24277a860b4986805d481
Source dataset
uspto-grants-2006_05
Patent number
US07053214B2

Reaction notes

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