Methyl 4-oxobutyrate → Methyl 4-((tert-butylsulfinyl)imino)butanoate

HRID 594327

反応式

HRID 594327 の反応式
O=[CH:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH3:9][C:10]([S:13]([NH2:15])=[O:14])([CH3:12])[CH3:11]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[C:10]([S:13]([N:15]=[CH:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])=[O:14])([CH3:12])([CH3:11])[CH3:9]

参加物

5

反応物 2

HCID 83779Methyl 4-oxobutyrateHCID 3382465Tert-Butanesulfinamide

生成物 1

HCID 86695623Methyl 4-((tert-butylsulfinyl)imino)butanoate

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of commercially available methyl 4-oxobutanoate (4.454 g; 38.36 mmol) in DCM (90 ml) was treated with 2-methylpropane-2-sulfinamide (4.650 g; 38.36 mmol) and with anh. CuSO4 (12.246 g; 76.73 mmol). The resulting heterogeneous mixture was further stirred at rt, under nitrogen, for 12 h. The resulting grey mixture was then filtered over a short pad of celite, and the separated solids were further washed with DCM. The obtained orange filtrate was concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded methyl 4-((tert-butylsulfinyl)imino)-butanoate as a yellow oil. LC-MS (conditions A): tR=0.56 min.; [M+H]+: 220.40 g/mol.

後処理

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

出典と根拠

ORDレコード
ord-9b9bd8699f6741a8b2f15b36619f56ba
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

関連ノート

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