Lithium Hydroxide → HCID 67227975, compound

HRID 624446Notes

Reaction equation

HRID 624446 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[CH:20]=[C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH2:33][CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30][C:29]=4[C:36]4[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=4)[CH2:23][CH2:22]3)[CH:18]=[CH:17][C:12]=2[C:13]([O:15]C)=[O:14])[CH:5]=[N:6][C:7]=1[NH:8][CH3:9].[Li+].[OH-]>O1CCCC1.CO.ClCCl.O>[Cl:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[CH:20]=[C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH2:33][CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30][C:29]=4[C:36]4[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=4)[CH2:23][CH2:22]3)[CH:18]=[CH:17][C:12]=2[C:13]([OH:15])=[O:14])[CH:5]=[N:6][C:7]=1[NH:8][CH3:9]

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 67226896HCID 67226896, compound

Product 1

HCID 67227975HCID 67227975, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of EXAMPLE 377G (0.295 g) in tetrahydrofuran (5 mL) and methanol (2 mL) was added 1.0M aqueous LiOH (1.452 mL) and the reaction was heated to 55° C. After stirring for 3 hours, the reaction was cooled, diluted with dichloromethane (75 mL) and water (15 mL) and quenched with 1N aqueous HCl (1.45 mL). The organic layer was separated, washed with brine (15 mL), dried over magnesium sulfate, filtered, and concentrated to provide the title compound.

Workup

  1. temperaturethe reaction was cooled
  2. customquenched with 1N aqueous HCl (1.45 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (15 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-73b938fbdbf04fe383c2e9a797053039
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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