Lithium Hydroxide → HCID 86584072, compound

HRID 843739Notes

Reaction equation

C([O:3][C:4](=[O:40])[C@@H:5]([NH:36][C:37](=[O:39])[CH3:38])[CH2:6][NH:7][C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:35])[CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH2:21][CH2:20]2)[CH2:11]1)=[O:9])C.[OH-].[Li+].OS([O-])(=O)=O.[K+]>C(O)C.O1CCCC1.O>[CH2:28]([O:27][C:25]([N:22]1[CH2:23][CH2:24][CH:19]([CH2:18][CH2:17][C:16]([N:12]2[CH2:13][CH2:14][CH2:15][C@@H:10]([C:8]([NH:7][CH2:6][C@H:5]([NH:36][C:37](=[O:39])[CH3:38])[C:4]([OH:40])=[O:3])=[O:9])[CH2:11]2)=[O:35])[CH2:20][CH2:21]1)=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-[(R)-1-{3-(1-benzyloxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S) -acetylamino-β-alanine ethyl ester (130 mg) in a mixture of ethanol (1.5 ml) and tetrahydrofuran (1.5 ml) was added a solution of lithium hydroxide (11 mg) in water (1.5 ml) under stirring at 0° C. After stirring at ambient temperature for 1 hour, the mixture was acidified with 10% 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-benzyloxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-acetylamino-β-alanine as an oil (67 mg).

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-f2c06ee61f644159b8a7990e36626df6
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380215B1

Reaction notes

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