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p-Bromobenzenesulfonyl chloride → (1aR,3aR,5R,7aR,15aS,Z)-methyl 5-(4-bromophenylsulfonyloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

HRID 926010
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HRID 926010 반응식
[OH:1][C@@H:2]1[CH2:27][CH2:26][C@H:5]2[C:6](=[O:25])[N:7]([CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][C@@H:14]3[CH2:19][C@@:15]3([C:20]([O:22][CH3:23])=[O:21])[NH:16][C:17](=[O:18])[C@@H:4]2[CH2:3]1.[Br:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([O:1][C@@H:2]2[CH2:27][CH2:26][C@H:5]3[C:6](=[O:25])[N:7]([CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][C@@H:14]4[CH2:19][C@@:15]4([C:20]([O:22][CH3:23])=[O:21])[NH:16][C:17](=[O:18])[C@@H:4]3[CH2:3]2)(=[O:37])=[O:36])=[CH:31][CH:30]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 69915043(1aR,3aR,5R,7aR,15aS,Z)-methyl 5-hydroxy-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

생성물 1

HCID 88050650(1aR,3aR,5R,7aR,15aS,Z)-methyl 5-(4-bromophenylsulfonyloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매2회

실험 절차

To a mixture of compound 43 (0.13 mmol), TEA (0.39 mmol), and DMAP (0.009 mmol) in anhydrous DCM (0.3 mL) was added 4-bromobenzenesulfonyl chloride (0.17 mmol) in DCM (0.15 mL) dropwise. The reaction mixture was stirred at room temperature under nitrogen for 16 hrs. The crude material was washed sequentially with 0.5N HCl and 2.5% NaHCO3. The organics were concentrated to yield compound 44 as a yellow oil in a quantitative yield. MS (ESI, EI+): m/z=598 (MH+).

후처리

  1. washThe crude material was washed sequentially with 0.5N HCl and 2.5% NaHCO3
  2. concentrationThe organics were concentrated

출처 및 근거

ORD 기록
ord-72edad27e9154592ae93de74eedfed18
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284307B2

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