Lithium hydroxide, monohydrate → HCID 178436414, compound

HRID 2099749Notes

Reaction equation

HRID 2099749 reaction equation
C[O:2][C:3](=[O:38])[CH:4]([NH:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([N:27]2[CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][C:28]2=[O:37])[CH2:23][CH2:22]1)=[O:20])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH2:15][CH3:16])[CH:14]=1)[NH:11][N:10]=[C:9]2[CH3:17].O1CCCC1.CO.O.[OH-].[Li+]>O>[CH2:15]([C:13]1[CH:14]=[C:6]([CH2:5][CH:4]([NH:18][C:19]([N:21]2[CH2:22][CH2:23][CH:24]([N:27]3[CH2:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[NH:29][C:28]3=[O:37])[CH2:25][CH2:26]2)=[O:20])[C:3]([OH:38])=[O:2])[CH:7]=[C:8]2[C:12]=1[NH:11][N:10]=[C:9]2[CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21899815MeOH tetrahydrofuranHCID 178436415HCID 178436415, compound

Product 1

HCID 178436414HCID 178436414, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of (±)-3-(7-ethyl-3-methyl-1H-indazol-5-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester (0.94 g, 1.81 mmol) in 1:1 tetrahydrofuran/methanol (30 mL) at room temperature was treated with a solution of lithium hydroxide monohydrate in water (10 mL). The solution was stirred at room temperature for 1 hand the solvents evaporated. The resultant residue was diluted with water (10 mL) and the pH adjusted to ca. 1 with 1N hydrochloric acid. The resultant white suspension was stored at 4° C. overnight and the product was collected by filtration, washed by a small amount of water and dried in vacuo for several hours to give 0.82 g (90%) of the desired product. LC/MS: tR=1.57 min, 505.29 (MH)+.

Workup

  1. customevaporated
  2. additionThe resultant residue was diluted with water (10 mL)
  3. filtrationthe product was collected by filtration
  4. washwashed by a small amount of water
  5. customdried in vacuo for several hours

Sources & evidence

ORD record
ord-d8f9e6480916439da94d09e43ab3f84f
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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