Lithium Hydroxide → HCID 86707798, compound

HRID 2174388Notes

Reaction equation

HRID 2174388 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH2:19][C:18]([C:24]4[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=4)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=3)=[CH:11][C:10]=2[Cl:33])[CH2:6]1)=[O:4].[OH-].[Li+]>C1COCC1.CO.O>[Cl:33][C:10]1[CH:11]=[C:12]([C:15]2[CH2:19][C:18]([C:24]3[CH:25]=[C:26]([Cl:32])[C:27]([Cl:31])=[C:28]([Cl:30])[CH:29]=3)([C:20]([F:22])([F:23])[F:21])[O:17][N:16]=2)[CH:13]=[CH:14][C:9]=1[N:7]1[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:8]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86707797HCID 86707797, compound

Product 1

HCID 86707798HCID 86707798, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a stirred suspension of 1-{2-Chloro-4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid methyl ester (Preparation 13, 0.55 g, 1.086 mmol) in THF:MeOH:H2O (1:1:1, 9 mL) was added lithium hydroxide (0.228 g, 5.43 mmol) at room temperature. Resulting reaction mixture was stirred at room temperature for 18 hours. After consumption of starting material, reaction mixture was concentrated in vacuo; acidified with 1N HCl up to pH ˜5. Acidified aqueous layer was extracted with ethyl acetate (5×20 mL). Combined organic layer was dried over sodium sulphate and evaporated under reduced pressure and was triturated with n-pentane (25 mL) to afford off white solid (0.4 g, 74%). 1H NMR (400 MHz, DMSO-d6) δ: 3.45-3.50 (m, 1H), 4.12-4.16 (m, 2H), 4.26-4.33 (m, 4H), 6.67 (d, 1H, J=9.04 Hz), 7.51-7.53 (m, 2H), 7.81 (s, 2H), 12.75 (bs, 1H); LC-MS (M+H): =528.80.

Workup

  1. customResulting
  2. customreaction mixture
  3. customAfter consumption of starting material, reaction mixture
  4. concentrationwas concentrated in vacuo
  5. extractionAcidified aqueous layer was extracted with ethyl acetate (5×20 mL)
  6. dry with materialCombined organic layer was dried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customwas triturated with n-pentane (25 mL)

Sources & evidence

ORD record
ord-3eefa9196b3c41b583c449e9538bd7b2
Source dataset
uspto-grants-2015_06
Patent number
US09061013B2

Reaction notes

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