Ammonium Chloride → Methyl 5-(1,1-dimethylethylsulfinamido)-5-(2-methoxynaphthalen-1-yl)pentanoate

HRID 594363Notes

Reaction equation

HRID 594363 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].[Li]CCCC.[C:19]([S:23]([N:25]=[CH:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[O:24])([CH3:22])([CH3:21])[CH3:20].[NH4+].[Cl-]>C1COCC1.O.CCOCC>[CH3:21][C:19]([CH3:22])([S:23]([NH:25][CH:26]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13])[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[O:24])[CH3:20]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 728601-Bromo-2-methoxynaphthaleneHCID 74336636Methyl 5-((tert-butylsulfinyl)imino)pentanoateHCID 178418339Butyllithium

Product 1

HCID 69082394Methyl 5-(1,1-dimethylethylsulfinamido)-5-(2-methoxynaphthalen-1-yl)pentanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A cooled (−78° C.) solution of commercially available 1-bromo-2-methoxynaphthalene (0.839 g; 2.14 mmol) in anh. THF (20 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.35 ml; 2.16 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 5-((tert-butylsulfinyl)imino)pentanoate (0.500 g; 2.14 mmol) in anh. THF (2 ml) was then added to the cooled reaction mixture, and stirring at −78° C. was continued for 30 min. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (35 ml), Et2O (75 ml) and water (20 ml). The separated organic layer was then washed with brine (30 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=15/1) afforded methyl 5-(1,1-dimethylethylsulfinamido)-5-(2-methoxynaphthalen-1-yl)pentanoate as a yellow oil. LC-MS (conditions A): tR=0.83 min. and [M+H]+: 391.93 g/mol.

Workup

  1. stirringstirring at −78° C.
  2. waitwas continued for 30 min
  3. customThe resulting reaction mixture
  4. washThe separated organic layer was then washed with brine (30 ml)
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (DCM/MeOH=15/1)

Sources & evidence

ORD record
ord-1533716df6f3407faf8f810d4fada3d5
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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