Lithium Hydroxide → HCID 22394458, compound

HRID 460001Notes

Reaction equation

HRID 460001 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]1[CH:19]=[C:18]([C:20]3[S:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[O:17][N:16]=1)[C:9]([C:26](=[O:37])[NH:27][CH:28]1[CH2:33][CH2:32][N:31]([CH:34]([CH3:36])[CH3:35])[CH2:30][CH2:29]1)=[CH:8]2)=[O:4].[Li+].[OH-]>C1COCC1.CO>[Cl:25][C:22]1[S:21][C:20]([C:18]2[O:17][N:16]=[C:15]([CH2:14][N:10]3[C:11]4[C:7](=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:13][CH:12]=4)[CH:8]=[C:9]3[C:26](=[O:37])[NH:27][CH:28]3[CH2:33][CH2:32][N:31]([CH:34]([CH3:35])[CH3:36])[CH2:30][CH2:29]3)[CH:19]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 20801203HCID 20801203, compound

Product 1

HCID 22394458HCID 22394458, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 8.8 g 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-indole-5-carboxylic acid methyl ester in 200 ml THF and 100 ml methanol 58.5 ml of a 1 M aqueous LiOH solution were added and the mixture was heated to 70° C. for 4 h. After cooling to RT the organic solvents were removed under reduced pressure and the remaining aqueous solution was acidified with half concentrated HCl to pH 2. The precipitated product was collected by filtration. Yield: 7.9 g.

Workup

  1. temperatureAfter cooling to RT the organic solvents
  2. customwere removed under reduced pressure
  3. filtrationThe precipitated product was collected by filtration

Sources & evidence

ORD record
ord-1c6fc34bce61470ebec0e2a3a264cf56
Source dataset
uspto-grants-2007_03
Patent number
US07196103B2

Reaction notes

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