Lithium Hydroxide → HCID 67227975, compound

HRID 1043191Notes

Reaction equation

HRID 1043191 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-fae29ba6f5b64266bc53b04070552db2
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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