p-Bromobenzenesulfonyl chloride → HCID 86642249、化合物

HRID 1517174ノート

反応式

HRID 1517174 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@@H:26]([OH:28])[CH2:27][C@H:21]2[C:20](=[O:29])[NH:19][C@:18]2([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:30][C@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N2CCN(CC2)C1.[Br:44][C:45]1[CH:50]=[CH:49][C:48]([S:51](Cl)(=[O:53])=[O:52])=[CH:47][CH:46]=1>C1(C)C=CC=CC=1>[Br:44][C:45]1[CH:50]=[CH:49][C:48]([S:51]([O:28][C@@H:26]2[CH2:25][N:22]3[C:23](=[O:24])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][C@@H:17]4[CH2:30][C@@:18]4([C:31]([O:33][CH2:34][CH3:35])=[O:32])[NH:19][C:20](=[O:29])[C@@H:21]3[CH2:27]2)(=[O:53])=[O:52])=[CH:47][CH:46]=1

参加物

5

反応物 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 9237DabcoHCID 57384485HCID 57384485、化合物

生成物 1

HCID 86642249HCID 86642249、化合物収率 87%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A solution of (2S,6S,13aS,14aR,16aS,Z)-ethyl 6-(tert-butoxycarbonylamino)-2-hydroxy-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (22.1 g, 44.8 mmol) and DABCO (8.5 g, 76.7 mmol) in toluene (88 mL) may be stirred at room temperature. To this solution may be added a solution of 4-bromobenzene-1-sulfonyl chloride 17.2 g, 67.2 mmol) in toluene (44 mL). After the addition is complete the reaction mixture can be quenched with 10% aqueous sodium carbonate (110 mL) and the mixture stirred for 15 min. Tetrahydrofuran (44 mL) can be added and the mixture is washed with 0.5 M HCl, water, and then saturated aqueous sodium chloride. The organic layer may be dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure and dried to provide the title compound (27.7 g, 87% yield), which may be used without further purification.

後処理

  1. additionAfter the addition
  2. customcan be quenched with 10% aqueous sodium carbonate (110 mL)
  3. additionTetrahydrofuran (44 mL) can be added
  4. washthe mixture is washed with 0.5 M HCl, water
  5. dry with materialThe organic layer may be dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customdried

出典と根拠

ORDレコード
ord-a21b6d3b66794b61bbb9cd10eb5744fd
出典データセット
uspto-grants-2012_07
特許番号
US08232246B2

反応ノート

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