Ethanol → HCID 66585108, compound

HRID 1630033Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 1.24 g (3.00 mmol) of 2-tert-butyl 8-ethyl 6-cyano-7-(3-fluorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxylate in 15 ml of a mixture of ethanol, water and tetrahydrofuran (1:1:1) is added 0.086 g (3.6 mmol) of lithium hydroxide, and the mixture is heated at 60° C. for 1 day. The mixture is then taken up in 60 ml of dichloromethane and is acidified by addition of aqueous 1N sulfuric acid. The organic phase is separated out and dried over sodium sulfate, and the solvent is evaporated off under reduced pressure to give a solid, which is triturated in acetonitrile to give 1.07 g of 2-(tert-butyloxycarbonyl)-6-cyano-7-(3-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid in the form of a white powder.

Workup

customThe organic phase is separated out
dry with materialdried over sodium sulfate
customthe solvent is evaporated off under reduced pressure
customto give a solid, which
customis triturated in acetonitrile

Sources & evidence

ORD record: ord-208c3080f89049548893a31503592c34
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791119B2

Reaction notes

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