Lithium hydroxide, monohydrate → HCID 69529836, compound

HRID 1814436Notes

Reaction equation

HRID 1814436 reaction equation
O.[OH-].[Li+].[I-:4].[C:5]1([NH:11][C:12](=[O:40])[NH:13][CH2:14][CH2:15][CH2:16][NH+:17]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([O:29]C)=[O:28])=[CH:23][CH:22]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O.CO>[I-:4].[C:5]1([NH:11][C:12](=[O:40])[NH:13][CH2:14][CH2:15][CH2:16][NH+:17]([CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=2)[CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69529775HCID 69529775, compound

Product 1

HCID 69529836HCID 69529836, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Lithium hydroxide monohydrate (4 mg, 0.095 mmol) was added to a solution of [3-(phenylureido)propyl][2-(4 chlorophenyl)ethyl][4-(methoxycarbonyl)benzyl]ethylammonium iodide (28 mg, 0.044 mmol) in 10% water/methanol (1.3 ml). After stirring at RT for 26 h, the reaction mixture was concentrated under vacuum to dryness. The residue was adsorbed on a plate of silica gel and then developed with 33% methanol/chloroform to afford [3-(phenylureido)propyl][2-(4-chlorophenyl)ethyl][4-(carboxy)benzyl]ethylammonium iodide (19 mg, 70%): MS(ES+) m/e 496 [M-I]+; 1H NMR (400 MHz, CD3OD) δ 8.01 (d, J=8.3 Hz, 2H), 7.53 (d, J=8.3 Hz, 2H), 7.38 (m, 2H), 7.30 (m, 4H), 7.24 (m, 2H), 6.97 (m, 1H), 4.59 (s, 2H), 3.31 (m, 8H), 3.15 (m, 2H), 2.15 (m, 2H), 1.48 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum to dryness

Sources & evidence

ORD record
ord-e640ee6bb7074d4e991557337a150e3f
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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