Lithium Hydroxide → (S)-3-(4-but-2-ynyloxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoic acid

HRID 517498Notes

Reaction equation

HRID 517498 reaction equation
[OH-].[Li+].[CH2:3]([O:7][C:8]1[CH:32]=[CH:31][C:11]([C:12]([NH:14][CH2:15][C@H:16]([N:21]2[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[C:17]([O:19]C)=[O:18])=[O:13])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6]>O1CCCC1.O>[CH2:3]([O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][CH2:15][C@H:16]([N:21]2[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[C:17]([OH:19])=[O:18])=[O:13])=[CH:31][CH:32]=1)[C:4]#[C:5][CH3:6]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67056862methyl (S)-3-(4-but-2-ynyloxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoate

Product 1

HCID 67056877(S)-3-(4-but-2-ynyloxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoic acidYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.1 ml (2.1 mmol) of an aqueous solution of lithium hydroxide having a concentration of 1N are added to a solution of 610 mg (1.4 mmol) of methyl (S)-3-(4-but-2-ynyloxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoate in 12 ml of tetrahydrofuran and 2 ml of water. The reaction medium is stirred at ambient temperature for 18 h then the solvents are concentrated under vacuum. The mixture is brought to pH=6 by addition of 2.5 ml of an aqueous solution of hydrochloric acid having a concentration of 1N. The solid which precipitates is filtered, rinsed with water then with diethyl ether, and dried under vacuum. 420 mg (72%) of (S)-3-(4-but-2-ynyloxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoic acid are obtained in the form of a white solid.

Workup

  1. concentrationthe solvents are concentrated under vacuum
  2. additionThe mixture is brought to pH=6 by addition of 2.5 ml of an aqueous solution of hydrochloric acid having a concentration of 1N
  3. customThe solid which precipitates
  4. filtrationis filtered
  5. washrinsed with water
  6. dry with materialwith diethyl ether, and dried under vacuum

Sources & evidence

ORD record
ord-9f941439b17b4e35a692513ad82e8aac
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

Loading…