Triethylamine → 4-chloro-N-(1-diazo-2-oxopentan-3-yl)-N-(pent-1-yn-3-yl)benzenesulfonamide

HRID 15727

反応式

HRID 15727 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH:17]([CH2:21][CH3:22])[C:18]([OH:20])=O)[CH:12]([CH2:15][CH3:16])[C:13]#[CH:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[N+:38](=[CH2:40])=[N-:39]>CCOCC.CC(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH:17]([CH2:21][CH3:22])[C:18](=[O:20])[CH:40]=[N+:38]=[N-:39])[CH:12]([CH2:15][CH3:16])[C:13]#[CH:14])(=[O:10])=[O:9])=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 9550DiazomethaneHCID 62365Isobutyl chloroformateHCID 593423732-(4-chloro-N-(pent-1-yn-3-yl)phenylsulfonamido)-butanoic acid

生成物 1

HCID 722595874-chloro-N-(1-diazo-2-oxopentan-3-yl)-N-(pent-1-yn-3-yl)benzenesulfonamide

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
-30 °C

実験手順

To a solution of the compound 60 (498 mg, 1.45 mmol) in 7.5 mL of Et2O were added sequentially 0.24 mL of triethylamine (1.2 eq), 0.23 mL of isobutyl chloroformate (1.2 eq) at −30° C. After being stirred at −30° C. for 15 min, diazomethane (prepared by mixing MNNG and KOH in diethyl ether) (excess) was added to the above mixture at 0° C. and stirred there for 5 hours. Glacial HOAc (1.5 mL) was added to destroy the excess diazomethane and the solution was extracted with EtOAc. The organic phase was washed with sat NaHCO3, water, brine and dried (MgSO4). LCMS 368.1 (M+1).

後処理

  1. stirringstirred there for 5 hours
  2. customto destroy the excess diazomethane
  3. extractionthe solution was extracted with EtOAc
  4. washThe organic phase was washed with sat NaHCO3, water, brine
  5. dry with materialdried (MgSO4)

出典と根拠

ORDレコード
ord-c6a04bb7504c4ce18d8cc8e65ca5dd39
出典データセット
uspto-grants-2010_06
特許番号
US07732609B2

関連ノート

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