Lithium Hydroxide → HCID 67227872, compound

HRID 2045112Notes

Reaction equation

HRID 2045112 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][C:11]([F:15])([F:14])[CH2:10][C:9]=2[CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[C:25]([O:33][C:34]4[CH:42]=[CH:41][CH:40]=[C:39]5[C:35]=4[CH:36]=[N:37][N:38]5[C:43]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH:24]=3)[CH2:19][CH2:18]2)=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1.CO.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][CH2:12][C:11]([F:15])([F:14])[CH2:10][C:9]=2[CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[C:25]([O:33][C:34]4[CH:42]=[CH:41][CH:40]=[C:39]5[C:35]=4[CH:36]=[N:37][N:38]5[C:43]([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)([C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=4)[C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=4)[CH:24]=3)[CH2:19][CH2:18]2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 67226729HCID 67226729, compound

Product 1

HCID 67227872HCID 67227872, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of EXAMPLE 521G (2.51 g) in tetrahydrofuran (30 mL) and methanol (10 mL) was added lithium hydroxide (1.0M, 10 mL) and the solution heated to 60° C. After 4 hours the reaction was cooled, diluted with dichloromethane (150 mL) and quenched with 1N aqueous HCl (10 mL) and water (30 mL). The organic layer was washed with brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 120 g) eluting with a gradient of 0.25% to 2.5% methanol/dichloromethane over 40 minutes gave the title compound.

Workup

  1. temperatureAfter 4 hours the reaction was cooled
  2. customquenched with 1N aqueous HCl (10 mL) and water (30 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washSilica gel chromatography (Reveleris 120 g) eluting with a gradient of 0.25% to 2.5% methanol/dichloromethane over 40 minutes

Sources & evidence

ORD record
ord-469921b721a04c5eb845abec7a82a966
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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