p-Bromobenzenesulfonyl chloride → HCID 86642249, 화합물

HRID 1517174노트

반응식

HRID 1517174 반응식
[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

참가 물질

5

반응물 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 9237DabcoHCID 57384485HCID 57384485, 화합물

생성물 1

HCID 86642249HCID 86642249, 화합물수율 87%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a21b6d3b66794b61bbb9cd10eb5744fd
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232246B2

반응 노트

불러오는 중…