Hydrochloric Acid → Methyl 4-amino-4-(2,4-dimethoxypyridin-3-yl)-2-methylbutanoate

HRID 594362Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([CH:9]([NH:18]S(C(C)(C)C)=O)[CH2:10][CH:11]([CH3:17])[C:12]([O:14][CH2:15]C)=[O:13])=[C:7]([O:25][CH3:26])[CH:6]=[CH:5][N:4]=1.Cl.O1CCOCC1>CO>[NH2:18][CH:9]([C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][C:7]=1[O:25][CH3:26])[CH2:10][CH:11]([CH3:17])[C:12]([O:14][CH3:15])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

A cooled (0° C.) solution of ethyl 4-(2,4-dimethoxypyridin-3-yl)-4-(1,1-dimethylethylsulfinamido)-2-methylbutanoate (0.709 g; 1.83 mmol) in MeOH (15 ml) was treated dropwise with a solution of 4 M HCl in 1,4-dioxane (0.92 ml; 3.67 mmol). The resulting mixture was further stirred at 0° C., under nitrogen, for 10 min., and then at rt for 30 min. The reaction mixture was then concentrated to dryness under reduced pressure and the oily residue was further dried under HV to give the chlorhydrate salt of methyl 4-amino-4-(2,4-dimethoxypyridin-3-yl)-2-methylbutanoate. LC-MS (conditions B): tR=0.45 min. and [M+H]+: 269.33 g/mol; tR=0.47 min. and [M+H]+: 269.33 g/mol (mixture of diastereoisomers).

Workup

waitat rt for 30 min
concentrationThe reaction mixture was then concentrated to dryness under reduced pressure
customthe oily residue was further dried under HV

Sources & evidence

ORD record: ord-62ecc8d9c74c425d8f1c115510cafebe
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242970B2

Reaction notes

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