Lithium Hydroxide → HCID 66870897, compound

HRID 874557Notes

Reaction equation

[OH-].[Li+].[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH2:18][C@H:19]([N:24]2[CH2:29][CH2:28][N:27]([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:26][CH2:25]2)[C:20]([O:22]C)=[O:21])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6]>O1CCCC1>[CH2:3]([O:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([NH:17][CH2:18][C@H:19]([N:24]2[CH2:25][CH2:26][N:27]([S:30]([CH3:33])(=[O:31])=[O:32])[CH2:28][CH2:29]2)[C:20]([OH:22])=[O:21])(=[O:16])=[O:15])=[CH:12][CH:13]=1)[C:4]#[C:5][CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

1.3 ml (1.3 mmol) of an aqueous solution of lithium hydroxide having a concentration of 1M are added to a solution of 400 mg (0.8 mmol) of methyl (S)-3-(4-but-2-ynyloxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoate diluted in 10 ml of tetrahydrofuran cooled beforehand to 0° C. The reaction medium is stirred at ambient temperature for 20 h. After evaporation to dryness, 1.5 ml of an aqueous solution of acetic acid having a concentration of 1M are added so as to obtain a pH=6. The product precipitates, and is filtered off, rinsed with water and then with diethyl ether and dried under vacuum. 340 mg (89%) of (S)-3-(4-but-2-ynyloxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoic acid are obtained in the form of a white solid.

Workup

customAfter evaporation to dryness, 1.5 ml of an aqueous solution of acetic acid having a concentration of 1M
additionare added so as
customto obtain a pH=6
customThe product precipitates
filtrationis filtered off
washrinsed with water
dry with materialwith diethyl ether and dried under vacuum

Sources & evidence

ORD record: ord-33aacb0efffc4150a18aad647928906c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980897B2

Reaction notes

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