Hydrochloric Acid → Methyl 3-amino-3-(4-butoxyphenyl)butanoate

HRID 1629799Notes

Reaction equation

HRID 1629799 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([NH:19]S(C(C)(C)C)=O)([CH3:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].Cl>CO>[NH2:19][C:12]([C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:11][CH:10]=1)([CH3:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86685892Methyl 3-(4-butoxyphenyl)-3-((tert-butylsulfinyl)amino)butanoate

Product 1

HCID 86685893Methyl 3-amino-3-(4-butoxyphenyl)butanoateYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of Intermediate 107B (1 g, 2.71 mmol) in MeOH (6 mL) was added 4 N HCl (3.38 mL, 13.53 mmol). The reaction was stirred at rt for 4 h. The reaction mixture was concentrated in vacuo and diluted with EtOAc. The organic layer was washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated to yield the desired product (700 mg, 97%) as a yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.38 (d, J=8.80 Hz, 2H), 6.86 (d, J=8.80 Hz, 2H), 3.95 (t, J=6.46 Hz, 2H), 3.59 (s, 3H), 1.73-1.80 (m, 2H), 1.53 (s, 2H), 1.45-1.52 (m, 2H), 1.19 (s, 3H), 0.98 (t, J=7.29 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2b81051b0a564aafba2f3fefd6f04a51
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

Loading…