홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

1,2-Dichloroethane → 4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxamide

HRID 1859287
노트
인쇄 미리보기

반응식

HRID 1859287 반응식
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:30]=[CH:29][C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH:20]4[CH:25]([C:26]([OH:28])=O)[NH:24][CH2:23][CH2:22][S:21]4)(=[O:19])=[O:18])=[CH:13][CH:12]=3)=[CH:8][CH:7]=2)=[CH:2]1.[Si](O[NH2:49])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)CCl>ClCCl>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:30]=[CH:29][C:9]([O:10][C:11]3[CH:12]=[CH:13][C:14]([S:17]([CH:20]4[CH:25]([C:26]([NH2:49])=[O:28])[NH:24][CH2:23][CH2:22][S:21]4)(=[O:18])=[O:19])=[CH:15][CH:16]=3)=[CH:8][CH:7]=2)=[CH:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 111,2-DichloroethaneHCID 11737343O-(tert-Butyldiphenylsilyl)hydroxylamineHCID 865886704-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxylic acid

생성물 1

HCID 865886724-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxamide수율 14.5%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a solution of 3(S)-4-(4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxylic acid (293 mg, 0.62 mmol) and O-(tert-butyldiphenylsilyl)hydroxylamine (0.22 g, 0.8 mmol) in 5 mL of dichloromethane was added EDC (132 mg, 0.69 mmol). After 18 hours at 25° C., the mixture was partitioned between 1 N aq. sodium bisulfate and dichloromethane. The aqueous layer was extracted twice with dichloromethane, and the combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by chromatography on silica gel, eluting with a gradient from dichloromethane to 5% methanol in dichloromethane, to provide 3(S)-N-(tert-butyldiphenylsilyl)oxy-4-(4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxamide (40 mg, 8%). FAB+MS Calcd for M+Cs+ =859.1308 Obs 859.1274; 1HNMR (d6 -DMSO): δ10.81 (s, 1H), 8.17 (s, 1H), 7.74 (s, 1H), 7.67-7.61 (m, 8H), 7.45-7.30 (m, 6H), 7.10 (d, 2H, J=8.83 Hz), 7.00 (d, 2H, J=8.46 Hz), 6.94 (s, 1H), 4.06 (s, 1H), 3.95-3.89 (bm, 1H), 3.77-3.73 (bm, 1H), 2.87-2.78 (bm, 1H), 1.28 (s, 3H), 0.99 (s, 9H), 0.61 (s, 3H)

후처리

  1. customthe mixture was partitioned between 1 N aq. sodium bisulfate and dichloromethane
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with a gradient from dichloromethane to 5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-76bd95b4c8c743baaba41354f040773f
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06153757

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트