Lithium Hydroxide → HCID 67226937, compound

HRID 1043144Notes

Reaction equation

HRID 1043144 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[CH2:28][C:27]=4[C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=4)[CH2:21][CH2:20]3)[CH:16]=[CH:15][C:10]=2[C:11]([O:13]C)=[O:12])=[CH:4][C:3]=1[Cl:41].[OH-].[Li+]>O1CCCC1.CO.ClCCl.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:18]=[C:17]([N:19]3[CH2:20][CH2:21][N:22]([CH2:25][C:26]4[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[CH2:28][C:27]=4[C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=4)[CH2:23][CH2:24]3)[CH:16]=[CH:15][C:10]=2[C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[Cl:41]

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 67227481HCID 67227481, compound

Product 1

HCID 67226937HCID 67226937, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of EXAMPLE 318G (12.5 g) in tetrahydrofuran (50 mL) and methanol (25 mL) was added lithium hydroxide (1.0 M, 52.5 mL) and the reaction heated to 55° C. The reaction was stirred for 4 hours, cooled, diluted with dichloromethane (300 mL) and water (50 mL) and quenched with 1N aqueous HCl (1.0M, 50 mL). The organic layer was separated, washed with brine (100 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound.

Workup

  1. temperaturecooled
  2. customquenched with 1N aqueous HCl (1.0M, 50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b120e60170ed4f72981499124fff6314
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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