4-Methylmorpholine → benzenesulfonyl-acetic acid N'-[2-(4-iodo-phenyl)-acetyl]-hydrazide

HRID 602801노트

반응식

HRID 602801 반응식
[C:1]1([S:7]([CH2:10][C:11]([NH:13][NH2:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:15]C(C1C=CC=CC=1)C(O)=O.ON1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2N=N1.CN1CC[O:40][CH2:39][CH2:38]1.CCN=C=NCCCN(C)C.[NH4+].[Cl-]>C1COCC1>[I:15][C:30]1[CH:35]=[CH:34][C:33]([CH2:38][C:39]([NH:14][NH:13][C:11](=[O:12])[CH2:10][S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])=[O:40])=[CH:32][CH:31]=1

참가 물질

8

반응물 6

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 9943159Iodophenylacetic acidHCID 11378890Benzenesulfonyl-acetic acid hydrazide

생성물 1

HCID 67266905benzenesulfonyl-acetic acid N'-[2-(4-iodo-phenyl)-acetyl]-hydrazide수율 469.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of 1 g (4.7 mmol) of benzenesulfonyl-acetic acid hydrazide (example 74.1) in 4 mL of THF was treated with 391 mg (4.7 mmol) of iodophenylacetic acid, 126 mg (0.93 mmol) of 1-hydroxybenzotriazole and 2.8 g (28 mmol) of N-methylmorpholine. The mixture was stirred during 15 min at 0° C., treated with 1.25 g (6.5 mmol) of EDCI and stirred during 12 hrs. The crude was treated with diluted aqueous NH4Cl and extracted twice with EtOAc. Drying of the combined organic layers over Na2SO4, filtration and evaporation gave 2 g (93%) of benzenesulfonyl-acetic acid N′-[2-(4-iodo-phenyl)-acetyl]-hydrazide as a brown oil, MS: 266 (MH+)

후처리

  1. stirringstirred during 12 hrs
  2. extractionextracted twice with EtOAc
  3. dry with materialDrying of the combined organic layers over Na2SO4, filtration and evaporation

출처 및 근거

ORD 기록
ord-184aee9abcfc4afcbfcf236f9652ebda
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906546B2

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