Lithium hydroxide, monohydrate → HCID 22137609, compound

HRID 1827337Notes

Reaction equation

HRID 1827337 reaction equation
C([O:3][C:4](=[O:22])/[CH:5]=[CH:6]/[CH:7]=[CH:8]/[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)C.O[Li].O>CCO>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][CH:9](/[CH:8]=[CH:7]/[CH:6]=[CH:5]/[C:4]([OH:22])=[O:3])[CH2:10][CH2:11]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22137606HCID 22137606, compound

Product 1

HCID 22137609HCID 22137609, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of the above ethyl ester (22) (2.60 g, 8.4 mmol) in absolute EtOH (30 mL) was added LiOH—H2O (720 mg, 17 mmol, in 10 mL of water). The reaction was heated to 50° C. for 1 h, then concentrated to remove excess EtOH. After acidification with 5% citric acid (50 mL), the product was extracted with EtOAc (2×100 mL). The combined organic extracts were washed with brine (100 mL), dried (MgSO4) and concentrated to give a white solid (23) (2.32 g, 98%). 1H NMR (500 MHz, CDCL3) δ 7.31 (dd, J=15.5, 11.0 Hz, 1H), 6.18 (dd, J=15.5, 11.0 Hz, 1H), 6.08 (dd, J=15.5, 7.0 Hz, 1H), 5.80 (d, J=15.5 Hz, 1H), 4.10 (m, 2H), 2.75 (m, 2H), 2.25 (m, 1H), 1.70 (m, 2H) 1.44 (s, 9H), 1.33 (m, 2H); MS (ESI−) m/z 280.74 (M−H+).

Workup

  1. concentrationconcentrated
  2. customto remove excess EtOH
  3. extractionAfter acidification with 5% citric acid (50 mL), the product was extracted with EtOAc (2×100 mL)
  4. washThe combined organic extracts were washed with brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f8146bc3e03849fdb1e35d7b0d069292
Source dataset
uspto-grants-2006_05
Patent number
US07053214B2

Reaction notes

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