Lithium hydroxide, monohydrate → HCID 70186151, compound

HRID 1070351Notes

Reaction equation

HRID 1070351 reaction equation
[CH3:1][O:2][C:3](=[O:38])[C@H:4]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C:15]=2[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:26][CH:25]=2)=[CH:10][CH:9]=1)[NH2:5].[OH:39][Li].O>C1COCC1.CO.O>[NH4+:5].[OH-:2].[CH3:1][OH:2].[CH3:4][CH2:6][O:7][C:8]([CH3:13])=[O:39].[N:33]1([CH2:32][CH2:31][O:30][C:27]2[CH:26]=[CH:25][C:24]([CH2:23][C:15]3[C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[S:18][C:14]=3[C:11]3[CH:12]=[CH:13][C:8]([O:7][CH2:6][C@@H:4]([C:3]([OH:38])=[O:2])[NH2:5])=[CH:9][CH:10]=3)=[CH:29][CH:28]=2)[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 70186562HCID 70186562, compound

Product 2

HCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 70186151HCID 70186151, compoundYield 220.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

O-[4-[3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]phenyl]-L-serine methyl ester (21 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 3 h. The reaction mixture was concentrated under reduced pressure. Chromatography with NH4OH:MeOH:EtOAc (10:20:70) afforded the title compound (15 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-07faa2c51e614a06acb7ae9e2f344b33
Source dataset
uspto-grants-2001_06
Patent number
US06251921B1

Reaction notes

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