Hydrochloric Acid → Methyl 6-amino-6-(2,6-dimethoxyphenyl)hexanoate

HRID 594334Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]([NH:21]S(C(C)(C)C)=O)[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19]C)=[O:17].Cl.O1CCOCC1>CO>[NH2:21][CH:11]([C:4]1[C:5]([O:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

A cooled (0° C.) yellow solution of ethyl 6-(2,6-dimethoxyphenyl)-6-(1,1-dimethylethylsulfinamido)hexanoate (5.360 g; 13.41 mmol) in MeOH (100 ml) was treated dropwise with a solution of 4 M HCl in 1,4-dioxane (6.7 ml; 26.80 mmol). The resulting yellow mixture was further stirred at 0° C., under nitrogen, for 10 min., and then at rt for 1 h50. The obtained yellow solution 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-(2,6-dimethoxyphenyl)hexanoate as a yellow oil. LC-MS (conditions B): tR=0.62 min.; [M+H]+: 282.10 g/mol.

Workup

customat rt
concentrationThe obtained yellow solution was then concentrated to dryness under reduced pressure
customthe yellow oily residue was further dried under HV

Sources & evidence

ORD record: ord-391e4be3a84f4073bf5e8fbf08437067
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242970B2

Reaction notes

Loading…