Water → HCID 117653243, compound

HRID 1486514Notes

Reaction equation

HRID 1486514 reaction equation
[CH3:1][C:2]([CH3:34])([CH3:33])[C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([O:25]CC)=[O:24])=[C:19]([CH3:30])[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:31].O.O[Li].O>C1COCC1>[CH3:34][C:2]([CH3:1])([CH3:33])[C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([OH:25])=[O:24])=[C:19]([CH3:30])[CH:18]=2)([CH2:13][CH3:14])[CH2:15][CH3:16])=[CH:8][C:7]=1[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 89663476HCID 89663476, compound

Product 1

HCID 117653243HCID 117653243, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 5 (50.0 mg, 0.1066 mmol) was dissolved in THF (1.0 mL) and H2O (0.5 mL) and LiOH.H2O (9.0 mg, 0.2133 mmol, 2.0 equiv.) was added. After stirring for 2 h, the reaction was quenched by the addition of sat. aq. NH4Cl solution and diluted with H2O. The resulting mixture was extracted with EtOAc (×3), and the combined organic phases were dried over MgSO4 and concentrated in vacuo. The crude residue was purified by preparative tlc (1:5:94 AcOH/MeOH/CH2Cl2) to afford the title acid 6 (31.4 mg, 67%)

Workup

  1. customthe reaction was quenched by the addition of sat. aq. NH4Cl solution
  2. additiondiluted with H2O
  3. extractionThe resulting mixture was extracted with EtOAc (×3)
  4. dry with materialthe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative tlc (1:5:94 AcOH/MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-143288f17c5a4a0bba02104f365dfb0b
Source dataset
uspto-grants-2016_08
Patent number
US09428447B2

Reaction notes

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