Lithium Hydroxide → N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3-ethynyl-beta-alanine

HRID 843738Notes

Reaction equation

C([O:3][C:4](=[O:35])[CH2:5][CH:6]([C:33]#[CH:34])[NH:7][C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:32])[CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH2:11]1)=[O:9])C.[OH-].[Li+].OS([O-])(=O)=O.[K+]>O1CCCC1.C(O)C.O>[C:28]([O:27][C:25]([N:22]1[CH2:21][CH2:20][CH:19]([CH2:18][CH2:17][C:16]([N:12]2[CH2:13][CH2:14][CH2:15][C@@H:10]([C:8]([NH:7][CH:6]([C:33]#[CH:34])[CH2:5][C:4]([OH:35])=[O:3])=[O:9])[CH2:11]2)=[O:32])[CH2:24][CH2:23]1)=[O:26])([CH3:31])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3-ethynyl-β-alanine ethyl ester (1.38 g) in tetrahydrofuran (5 ml), ethanol (5 ml) and water (5 ml) was added lithium hydroxide (0.35 g) under stirring at 0° C. After stirring at ambient temperature for 1 hour, the mixture was acidified with 5% KHSO4 aqueous solution and extracted with ethyl acetate. The extract was washed with water, brine and dried over MgSO4, and evaporated in vacuo to give N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3-ethynyl-β-alanine (1.12 g).

Workup

stirringAfter stirring at ambient temperature for 1 hour
extractionextracted with ethyl acetate
washThe extract was washed with water, brine
dry with materialdried over MgSO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-b6b8c2a6619f4cb8ab5886c8684737ee
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380215B1

Reaction notes

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