Hydrochloric Acid → Ethyl 4-amino-4-(2,6-dimethoxyphenyl)-2-methylbutanoate

HRID 594338Notes

Reaction equation

HRID 594338 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:20]S(C(C)(C)C)=O)[CH2:12][CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl.O1CCOCC1>CO>[NH2:20][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][CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86695625Ethyl 4-(2,6-dimethoxyphenyl)-4-(1,1-dimethylethylsulfinamido)-2-methylbutanoate

Product 1

HCID 69085588Ethyl 4-amino-4-(2,6-dimethoxyphenyl)-2-methylbutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) orange solution of ethyl 4-(2,6-dimethoxyphenyl)-4-(1,1-dimethylethylsulfinamido)-2-methylbutanoate (9.210 g; 23.89 mmol) in MeOH (100 ml) was treated dropwise with a solution of 4 M HCl in 1,4-dioxane (11.95 ml; 47.80 mmol). The resulting orange mixture was further stirred at 0° C., under nitrogen, for 10 min., and then at rt for 3 h. 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 ethyl 4-amino-4-(2,6-dimethoxyphenyl)-2-methylbutanoate as an orange oil. LC-MS (conditions B): tR=0.62 min. and [M+H]+: 282.42 g/mol; tR=0.64 min. and [M+H]+: 282.42 g/mol (mixture of diastereoisomers). Due to transesterification, a reduced amount of methyl 4-amino-4-(2,6-dimethoxyphenyl)-2-methylbutanoate was also detected: tR=0.57 min. and [M+H]+: 268.40 g/mol.

Workup

  1. waitat rt for 3 h
  2. concentrationThe reaction mixture was then concentrated to dryness under reduced pressure
  3. customthe oily residue was further dried under HV

Sources & evidence

ORD record
ord-f41e48ec711c42e78c576c896774e6c7
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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