Lithium Hydroxide → (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-(4-methoxybenzoyl-amino)propanoic acid

HRID 517507Notes

Reaction equation

HRID 517507 reaction equation
[OH-].[Li+].[CH3:3][S:4]([N:7]1[CH2:12][CH2:11][N:10]([C@@H:13]([CH2:18][NH:19][C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:14]([O:16]C)=[O:15])[CH2:9][CH2:8]1)(=[O:6])=[O:5]>O1CCCC1.O>[CH3:3][S:4]([N:7]1[CH2:8][CH2:9][N:10]([C@@H:13]([CH2:18][NH:19][C:20](=[O:29])[C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[C:14]([OH:16])=[O:15])[CH2:11][CH2:12]1)(=[O:5])=[O:6]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86667906methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-(4-methoxybenzoyl-amino)propanoate

Product 1

HCID 67056979(S)-2-(4-methanesulphonylpiperazin-1-yl)-3-(4-methoxybenzoyl-amino)propanoic acidYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 ml (1 mmol) of an aqueous solution of lithium hydroxide having a concentration of 1N is added to a solution of 260 mg (0.7 mmol) of methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-(4-methoxybenzoyl-amino)propanoate in 8 ml of tetrahydrofuran and 1 ml of water. The reaction medium is stirred at ambient temperature for 20 h. The solvents are concentrated under vacuum, the reaction medium is brought to pH=6 with an aqueous solution of acetic acid having a concentration of 1N. The product precipitates and the residue is taken up in 10 ml of water and stirred for 1 h. The solid is filtered, rinsed with water and with diethyl ether then dried. 190 mg (76%) of (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-(4-methoxybenzoyl-amino)propanoic acid are obtained in the form of a white solid.

Workup

  1. concentrationThe solvents are concentrated under vacuum
  2. customThe product precipitates
  3. stirringstirred for 1 h
  4. filtrationThe solid is filtered
  5. washrinsed with water and with diethyl ether
  6. customthen dried

Sources & evidence

ORD record
ord-995b2a16237942b89cf256b5337c41db
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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