Hydrochloric Acid → Methyl 5-amino-5-(3,5-dimethoxypyridin-4-yl)pentanoate

HRID 594343Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([O:24][CH3:25])[C:8]=1[CH:9]([NH:17]S(C(C)(C)C)=O)[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].Cl.O1CCOCC1>CO>[NH2:17][CH:9]([C:8]1[C:7]([O:24][CH3:25])=[CH:6][N:5]=[CH:4][C:3]=1[O:2][CH3:1])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

A cooled (0° C.) yellow solution of methyl 5-(3,5-dimethoxypyridin-4-yl)-5-(1,1-dimethylethylsulfinamido)pentanoate (780 mg; 2.09 mmol) in MeOH (16 ml) was treated dropwise with a solution of 4 M HCl in 1,4-dioxane (1.05 ml; 4.20 mmol). The resulting yellow mixture was further stirred at 0° C., under nitrogen, for 10 min., and then at rt for 1 h. The reaction mixture was then concentrated to dryness under reduced pressure and the yellow oily residue was further dried under HV to give the chlorhydrate salt of methyl 5-amino-5-(3,5-dimethoxypyridin-4-yl)pentanoate as a beige solid. LC-MS (conditions B): tR=0.43 min.; [M+H]+: 269.02 g/mol.

Workup

waitat rt for 1 h
concentrationThe reaction mixture was then concentrated to dryness under reduced pressure
customthe yellow oily residue was further dried under HV

Sources & evidence

ORD record: ord-bd36fccb192a49e8a6996b25af8755f3
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242970B2

Reaction notes

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