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

HRID 15727

반응식

HRID 15727 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 3283Diethyl Ether용매

반응 조건

온도
-30 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c6a04bb7504c4ce18d8cc8e65ca5dd39
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732609B2

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