(R)-sec-butylamine → 3-[2-((R)-sec-Butylamino)-3,4-dioxo-cyclobut-1-enylamino]-6-chloro-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide

HRID 1669601

反応式

HRID 1669601 の反応式
[Cl:1][C:2]1[C:7]([S:8]([N:11]([O:13][CH3:14])[CH3:12])(=[O:10])=[O:9])=[C:6]([OH:15])[C:5]([NH:16][C:17]2[C:20](=O)[C:19](=[O:22])[C:18]=2[O:23]CC)=[CH:4][CH:3]=1.[NH2:26][C@@H:27]([CH2:29][CH3:30])[CH3:28]>C1COCC1>[C@H:27]([NH:26][C:20]1[C:19](=[O:22])[C:18](=[O:23])[C:17]=1[NH:16][C:5]1[C:6]([OH:15])=[C:7]([S:8]([N:11]([O:13][CH3:14])[CH3:12])(=[O:10])=[O:9])[C:2]([Cl:1])=[CH:3][CH:4]=1)([CH2:29][CH3:30])[CH3:28]

参加物

4

反応物 2

HCID 2724537(R)-sec-butylamineHCID 568442936-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide2 回

生成物 1

HCID 446291473-[2-((R)-sec-Butylamino)-3,4-dioxo-cyclobut-1-enylamino]-6-chloro-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of 6-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide (Intermediate A) (1 g, 2.56 mmol) in THF (20 ml) was added (R)-(−)-2-aminobutane (0.52 ml, 5.12 mmol). The reaction mixture was heated at 50° C. for 7 hours. The reaction mixture was concentrated in vacuo and dissolved in EtOAc. The EtOAc solution was washed with 1M HCl(aq) and brine. The EtOAc solution was dried (MgSO4) and concentrated in vacuo. The residue was crystallized from toluene to give a solid; [M+H]+ 418.2. 1H NMR (DMSO) 0.9 (3H, t, CH3), 1.2 (3H, d, CH3), 1.5 (2H, m), 3.0 (3H, s, CH3), 3.6 (3H, s, CH3), 4.0 (1H, m), 7.2 (1H, d), 8.1 (1H, d), 8.3 (1H, d), 9.4 (1H, s), 10.1 (1H, s).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOAc
  3. washThe EtOAc solution was washed with 1M HCl(aq) and brine
  4. dry with materialThe EtOAc solution was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from toluene
  7. customto give a solid

出典と根拠

ORDレコード
ord-3ceed3f422ed4632b77c318b1b988480
出典データセット
uspto-grants-2011_08
特許番号
US07989497B2

関連ノート

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