Lithium hydroxide, monohydrate → HCID 67444533, compound

HRID 1666555Notes

Reaction equation

HRID 1666555 reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:38])[CH2:8][CH2:9][N:10]([CH2:18][C:19]1[CH:37]=[CH:36][C:22]2[N:23]=[C:24]([NH2:35])[N:25]([CH2:26][C:27]3[C:32]([OH:33])=[CH:31][CH:30]=[C:29]([CH3:34])[N:28]=3)[C:21]=2[CH:20]=1)[C:11]1[CH:12]=[C:13]([CH3:17])[CH:14]=[CH:15][CH:16]=1)C>O.O1CCCC1>[NH2:35][C:24]1[N:25]([CH2:26][C:27]2[C:32]([OH:33])=[CH:31][CH:30]=[C:29]([CH3:34])[N:28]=2)[C:21]2[CH:20]=[C:19]([CH2:18][N:10]([C:11]3[CH:12]=[C:13]([CH3:17])[CH:14]=[CH:15][CH:16]=3)[CH2:9][CH2:8][C:7]([OH:38])=[O:6])[CH:37]=[CH:36][C:22]=2[N:23]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67441908HCID 67441908, compound

Product 1

HCID 67444533HCID 67444533, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide hydrate (0.00093 mol) was added to a solution of 3-{[2-amino-3-(3-hydroxy-6-methyl-pyridin-2-ylmethyl)-3H-benzoimidazol-5-ylmethyl]-m-tolylamino}-propionic acid ethyl ester (0.000464 mol) in a mixture of water (10 ml) and tetrahydrofuran (10 ml). The reaction was stirred at room temperature for 12 hours. The tetrahydrofuran was removed under reduced pressure and the solution was acidified to pH 4 with a 1N solution of HCl in water. The precipitate was filtered off, rinsed with water, then with diethyl ether and dried, yielding 0.157 g of 3-{[2-amino-3-(3-hydroxy-6-methyl-pyridin-2-ylmethyl)-3H-benzoimidazol-5-ylmethyl]-m-tolyl-amino}-propionic acid (76%, compound 161, melting point 165° C.).

Workup

  1. customThe tetrahydrofuran was removed under reduced pressure
  2. filtrationThe precipitate was filtered off
  3. washrinsed with water
  4. dry with materialwith diethyl ether and dried

Sources & evidence

ORD record
ord-4b9e6f5f320d470bb934ed83ff0ddb33
Source dataset
uspto-grants-2011_10
Patent number
US08044073B2

Reaction notes

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