Hydrochloric Acid → Ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate

HRID 1842983ノート

反応式

HRID 1842983 の反応式
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>CN(C=O)C.C(O)(C(F)(F)F)=O.[Mn]>[CH3:11][S:8]([NH:7][CH2:6][C:5]1[CH:12]=[CH:13][C:2]([CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 10807Ethyl 2-chloropropionateHCID 19027423N-[(4-bromophenyl)methyl]methanesulfonamide

生成物 1

HCID 70816013Ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate

試薬・触媒・溶媒 3

HCID 6422Trifluoroacetic acid触媒HCID 23930Manganese触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of N-(4-bromobenzyl)methanesulfonamide (675 mg, 2.555 mmol) in DMF were added ethyl 2-chloropropionate (0.42 mL), manganese (280 mg) and (2,2′-bipyridine)nickel(II)-dibromide (NiBr2bipy) (67 mg, 0.17885 mmol). TFA (1-2 drops) was added. The reaction mixture was stirred for 36 h at 60° C. After cooling down to room temperature, the mixture was hydrolyzed by 1N HCl and extracted with diethyl ether. The organic layer was dried (MgSO4) and filtered. The solvent was removed in vacuo. The crude product was purified by CC. Ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate (325 mg) was obtained.

後処理

  1. temperatureAfter cooling down to room temperature
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by CC

出典と根拠

ORDレコード
ord-5ea7c1f48b6941bf97aadf072c0b3928
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

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