Lithium Hydroxide → HCID 86693106, compound

HRID 575211Notes

Reaction equation

HRID 575211 reaction equation
C([O:9][CH:10]1[CH2:13][C:12]([C:15]#[C:16][C:17]2[C:18]([F:34])=[CH:19][C:20]3[O:26][CH2:25][CH2:24][N:23]4[CH:27]=[C:28]([C:30](=[O:32])[NH2:31])[N:29]=[C:22]4[C:21]=3[CH:33]=2)([OH:14])[CH2:11]1)(=O)C1C=CC=CC=1.[OH-].[Li+]>CO.O.ClCCl>[OH:14][C:12]1([C:15]#[C:16][C:17]2[C:18]([F:34])=[CH:19][C:20]3[O:26][CH2:25][CH2:24][N:23]4[CH:27]=[C:28]([C:30]([NH2:31])=[O:32])[N:29]=[C:22]4[C:21]=3[CH:33]=2)[CH2:11][CH:10]([OH:9])[CH2:13]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86693107HCID 86693107, compound

Product 1

HCID 86693106HCID 86693106, compoundYield 4.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-((2-carbamoyl-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-10-yl)ethynyl)-3-hydroxycyclobutyl benzoate (190 mg, crude product), lithium hydroxide (96 mg, 4.01 mmol) in methanol (0.5 mL) and water (1 mL) was stirred at room temperature overnight. The resulting solution was diluted with 20 mL of dichloromethane and 10 mL water. The organic layer was washed with 10 mL of brine. The organic was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (1:10). This resulted in 7 mg of the titled compound as a light yellow solid. This compound was isolated as a single unassigned diasteromer.

Workup

  1. washThe organic layer was washed with 10 mL of brine
  2. dry with materialThe organic was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5b3b23a650184718bc1104b5a52a537f
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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