Triethylamine → 6-Chloro-2-hydroxy-N-methoxy-3-[2-((R)-1-methoxymethyl-2-methyl-propylamino)-3,4-dioxo-cyclobut-1-enylamino]-N-methyl-benzenesulfonamide

HRID 1024559

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HRID 1024559 반응식
[CH2:1](N(CC)CC)C.[NH2:8][C@H:9]([CH:12]([CH3:14])[CH3:13])[CH2:10][OH:11].[Cl:15][C:16]1[C:21]([S:22]([N:25]([O:27][CH3:28])[CH3:26])(=[O:24])=[O:23])=[C:20]([OH:29])[C:19]([NH:30][C:31]2[C:34](=O)[C:33](=[O:36])[C:32]=2[O:37]CC)=[CH:18][CH:17]=1>CCO>[Cl:15][C:16]1[C:21]([S:22]([N:25]([O:27][CH3:28])[CH3:26])(=[O:23])=[O:24])=[C:20]([OH:29])[C:19]([NH:30][C:31]2[C:32](=[O:37])[C:33](=[O:36])[C:34]=2[NH:8][C@@H:9]([CH2:10][O:11][CH3:1])[CH:12]([CH3:14])[CH3:13])=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 6950587D-Valinol2회HCID 568442936-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide2회

생성물 1

HCID 446291496-Chloro-2-hydroxy-N-methoxy-3-[2-((R)-1-methoxymethyl-2-methyl-propylamino)-3,4-dioxo-cyclobut-1-enylamino]-N-methyl-benzenesulfonamide

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
85 °C

실험 절차

To a stirred solution of triethylamine (1.192 ml, 8.55 mmol) and (R)-2-Amino-3-methyl-butan-1-ol (Intermediate H) in EtOH (36 ml) was added 6-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide (Intermediate A) (1.67 g, 4.27 mmol). The reaction mixture was heated at 85° C. for 18 hours. The reaction mixture was concentrated in vacuo and dissolved in EtOAc. The EtOAc solution was washed with 1M HCl (aq) and NaHCO3 (aq). The NaHCO3 (aq) layer was extracted with EtOAc. The EtOAc layers were combined and concentrated in vacuo. The residue was purified using flash chromatography (0-10% MeOH in DCM) to furnish a brown solid [M+H]+ 462.0.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOAc
  3. washThe EtOAc solution was washed with 1M HCl (aq) and NaHCO3 (aq)
  4. extractionThe NaHCO3 (aq) layer was extracted with EtOAc
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. customto furnish a brown solid [M+H]+ 462.0

출처 및 근거

ORD 기록
ord-16d6a2464d914e778632e25b7c50c17e
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722925B2

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