Potassium Hydroxide → HCID 68388386, compound

HRID 529341Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][N:21]([C@@H:28]2[CH2:30][C@H:29]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)C(=O)C(F)(F)F)[CH2:16][CH2:15]1)[C:6]([O:8]C)=[O:7])#[N:2].[OH-].[K+:38]>CO.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][C@@H:28]2[CH2:30][C@H:29]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:16][CH2:15]1)[C:6]([O-:8])=[O:7])#[N:2].[K+:38]

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred solution of methyl 3-cyano-4-((4-((2,2,2-trifluoro-N-((trans)-2-phenylcyclopropyl)acetamido)methyl)piperidin-1-yl)methyl)benzoate (1.2 g, 2.402 mmol) in a mixture of methanol (15 mL) and water (2 mL) was added KOH (0.404 g, 7.21 mmol) at RT. Then the reaction mixture was stirred at 65° C. for 3 h. The reaction mixture was concentrated to afford (crude) potassium 3-cyano-4-((4-((((trans)-2-phenylcyclopropyl)amino)methyl)piperidin-1-yl)methyl)benzoate (1 g, 107% yield). This was used as such in the next step.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-00826c32756c414a94d69fa1657a442f
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346840B2

Reaction notes

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