Lithium hydroxide, monohydrate → HCID 57625191, compound

HRID 658985Notes

Reaction equation

HRID 658985 reaction equation
O.[OH-].[Li+].[CH2:4]([C:11]1[CH:12]=[CH:13][C:14]([C:17]#[C:18][C:19]2[CH:33]=[CH:32][C:22]([CH2:23][N:24]3[CH2:27][CH:26]([C:28]([O:30]C)=[O:29])[CH2:25]3)=[CH:21][C:20]=2[F:34])=[N:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1COCC1.O>[CH2:4]([C:11]1[CH:12]=[CH:13][C:14]([C:17]#[C:18][C:19]2[CH:33]=[CH:32][C:22]([CH2:23][N:24]3[CH2:27][CH:26]([C:28]([OH:30])=[O:29])[CH2:25]3)=[CH:21][C:20]=2[F:34])=[N:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57625192HCID 57625192, compound

Product 1

HCID 57625191HCID 57625191, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of lithium hydroxide hydrate (28.4 mg, 677 μmol) and methyl 1-(4-(2-(5-benzylpyridin-2-yl)ethynyl)-3-fluorobenzyl)azetidine-3-carboxylate (77.9 mg, 188 μmol) in THF (2.7 mL) and water (0.69 mL) was stirred at 25° C. for 3 h. The reaction mixture was then partially concentrated in vacuo (to remove THF), water (1.5 mL) was added, and the resulting solution was sonicated for 1 min. The reaction solution was subsequently acidified with 1.0N HCl (670 μL), brought to pH 6 with 1M Na2HPO4/NaH2PO4 phosphate buffer (1.0 mL), and sonicated. The resulting precipitate was collected by vacuum filtration, washed with water (3.0 mL), and dried in vacuo to provide 1-(4-(2-(5-benzylpyridin-2-yl)ethynyl)-3-fluorobenzyl)azetidine-3-carboxylic acid as a light yellow solid. MS (ESI) m/z: Calculated: 400.2; Observed: 401.1 (M++1).

Workup

  1. concentrationThe reaction mixture was then partially concentrated in vacuo (to remove THF), water (1.5 mL)
  2. additionwas added
  3. customthe resulting solution was sonicated for 1 min
  4. customsonicated
  5. filtrationThe resulting precipitate was collected by vacuum filtration
  6. washwashed with water (3.0 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-4b994f8d795f4faaa4389b70f5e65a40
Source dataset
uspto-grants-2011_12
Patent number
US08080542B2

Reaction notes

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