Lithium hydroxide, monohydrate → HCID 21713635, compound

HRID 650027Notes

Reaction equation

HRID 650027 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:44]=[CH:43][C:12]([CH2:13][C:14]3[C:15]4[CH:42]=[CH:41][CH:40]=[CH:39][C:16]=4[S:17][C:18]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][CH2:28][C:29]4[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][CH:30]=4)=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O[Li].O.[CH2:48]1C[O:51][CH2:50]C1.CO.O>>[NH4+:1].[OH-:8].[CH3:50][OH:51].[CH3:48][CH2:38][O:37][C:35]([CH3:32])=[O:36].[C:35]([C:32]1[CH:33]=[CH:34][C:29]([CH2:28][NH:27][CH2:26][CH2:25][C:22]2[CH:21]=[CH:20][C:19]([C:18]3[S:17][C:16]4[CH:39]=[CH:40][CH:41]=[CH:42][C:15]=4[C:14]=3[CH2:13][C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)=[CH:44][CH:43]=3)=[CH:24][CH:23]=2)=[CH:30][CH:31]=1)([OH:37])=[O:36]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21713607HCID 21713607, compoundHCID 21892291Methanol tetrahydrofuran water

Product 2

HCID 21713635HCID 21713635, compoundHCID 21901312Ethyl acetate methanol ammonium hydroxide

Procedure

3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]-2-[4-[2-(4-methoxycarbonylbenzylamino)ethyl]phenyl]benzo[b]thiophene (47 mg) was dissolved in THF:MeOH:H2O (3:1:1, 3 mL), treated with LiOH-H2O (5 mg) in one portion and allowed to stir at ambient temperature for 62 h. The reaction mixture was concentrated under reduced pressure. Chromatography with NH4OH:MeOH:EtOAc (5:10:85) afforded the title compound (32 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6a0d59972b624074b4bbab6765a924a7
Source dataset
uspto-grants-2001_08
Patent number
US06271227B1

Reaction notes

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