Lithium Hydroxide → HCID 89717546, compound

HRID 63728Notes

Reaction equation

HRID 63728 reaction equation
C[O:2][C:3](=[O:39])[C@@H:4]([NH:23][C:24](=[O:38])[C:25]1[C:30]([Cl:31])=[CH:29][C:28]([O:32][CH2:33][CH2:34][CH2:35][NH2:36])=[CH:27][C:26]=1[Cl:37])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:22])[C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:21])=[CH:8][CH:7]=1.[OH-].[Li+]>C1COCC1.O>[NH2:36][CH2:35][CH2:34][CH2:33][O:32][C:28]1[CH:27]=[C:26]([Cl:37])[C:25]([C:24]([NH:23][C@@H:4]([CH2:5][C:6]2[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])=[CH:10][CH:11]=2)[C:3]([OH:39])=[O:2])=[O:38])=[C:30]([Cl:31])[CH:29]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89719307(S)-2-[4-(3-aminopropoxy)-2,6-dichlorobenzoylamino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester

Product 1

HCID 89717546HCID 89717546, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-[4-(3-aminopropoxy)-2,6-dichlorobenzoylamino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester (5.8 g, 7.98 mmol,) in THF (200 mL) was added a solution of lithium hydroxide (2.4 g, 100 mmol) in water (30 mL) at room temperature. The mixture was stirred for 15 h at room temperature at which time TLC analysis of the mixture indicated the absence of starting material. Then, the solvent was removed by rotary evaporation and the residue was purified by an HPLC method to obtain 3.7 g (65% yield) of (S)-2-[4-(3-aminopropoxy)-2,6-dichlorobenzoylamino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid as a white solid. ES(+)-HRMS m/e calcd. for C26H23Cl4N3O5 (M+H)+ 598.0465, obsd. 598.0465.

Workup

  1. customThen, the solvent was removed by rotary evaporation
  2. customthe residue was purified by an HPLC method

Sources & evidence

ORD record
ord-cb19de002e244222bf1960fa6bcc3c3b
Source dataset
uspto-grants-2016_09
Patent number
US09447035B2

Reaction notes

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