Lithium hydroxide, monohydrate → Ethyl acetate methanol ammonium hydroxide

HRID 1387130Notes

Reaction equation

HRID 1387130 reaction equation
[CH3:1][O:2]C(=O)[C@H:4]([CH2:6][O:7][C:8]1[CH:13]=CC(C2SC3C=CC=CC=3C=2CC2C=CC(OCCN3CCCC3)=CC=2)=CC=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]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 70186562HCID 70186562, compound

Product 1

HCID 21901312Ethyl acetate methanol ammonium hydroxide

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-7997af2449fd4691ac4ed021ee240e24
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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