Tert-Butanesulfinamide → Ethyl 4-((tert-butylsulfinyl)imino)-2-methylbutanoate

HRID 594329Notes

Reaction equation

HRID 594329 reaction equation
[CH3:1][CH:2]([CH2:8][CH:9]=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:11][C:12]([S:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[C:12]([S:15]([N:17]=[CH:9][CH2:8][CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:16])([CH3:14])([CH3:13])[CH3:11]

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 13218106HCID 13218106, compound

Product 1

HCID 86695624Ethyl 4-((tert-butylsulfinyl)imino)-2-methylbutanoate

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A yellow solution of ethyl 2-methyl-4-oxobutanoate (35.16 mmol) in DCM (72 ml) was treated with 2-methylpropane-2-sulfinamide (4.261 g; 35.16 mmol) and with anh. CuSO4 (11.223 g; 70.32 mmol). The resulting beige heterogeneous mixture was further stirred at rt, under nitrogen, for 24 h. The resulting heterogeneous mixture was then filtered over a short pad of celite, and the separated solids were further washed with DCM. The obtained yellow filtrate was concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded ethyl 4-((tert-butylsulfinyl)imino)-2-methylbutanoate as a yellow oil. LC-MS (conditions B): tR=0.78 min.; [M+H]+: 248.38 g/mol.

Workup

  1. filtrationThe resulting heterogeneous mixture was then filtered over a short pad of celite
  2. washthe separated solids were further washed with DCM
  3. concentrationThe obtained yellow filtrate was concentrated to dryness under reduced pressure
  4. customPurification by FC (DCM/MeOH=25/1)

Sources & evidence

ORD record
ord-cf4f7d71003846b7834382c67e08e54a
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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