Hydrochloric Acid → Methyl 6-amino-6-(3,5-dimethoxypyridin-4-yl)hexanoate

HRID 594345Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([O:25][CH3:26])[C:8]=1[CH:9]([NH:18]S(C(C)(C)C)=O)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].Cl.O1CCOCC1>CO>[NH2:18][CH:9]([C:8]1[C:3]([O:2][CH3:1])=[CH:4][N:5]=[CH:6][C:7]=1[O:25][CH3:26])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

A cooled (0° C.) yellow solution of methyl 6-(3,5-dimethoxypyridin-4-yl)-6-(1,1-dimethylethylsulfinamido)hexanoate (506 mg; 1.30 mmol) in MeOH (9 ml) was treated dropwise with a solution of 4 M HCl in 1,4-dioxane (0.65 ml; 2.60 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 6-amino-6-(3,5-dimethoxypyridin-4-yl)hexanoate as a brown solid. LC-MS (conditions A): tR=0.36 min.; [M+H]+: 284.25 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-9afc0a74f9a24ae684328d59aee31bf1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242970B2

Reaction notes

Loading…