Triethyl(methoxycarbonylsulfamoyl)aminium → N-[(4aR,6R,8aS)-8a-(5-bromo-2-fluorophenyl)-6-(4-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

HRID 68421

반응식

HRID 68421 반응식
C([N+](CC)(CC)S(NC(=O)OC)(=O)=O)C.[C:16]([NH:24][C:25]1[S:26][CH2:27][C@@H:28]2[CH2:34][C@H:33]([C:35]([NH:37][CH:38]([CH3:41])[CH:39]=O)=[O:36])[O:32][CH2:31][C@:29]2([C:42]2[CH:47]=[C:46]([Br:48])[CH:45]=[CH:44][C:43]=2[F:49])[N:30]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Br:48][C:46]1[CH:45]=[CH:44][C:43]([F:49])=[C:42]([C@:29]23[CH2:31][O:32][C@@H:33]([C:35]4[O:36][CH:39]=[C:38]([CH3:41])[N:37]=4)[CH2:34][C@H:28]2[CH2:27][S:26][C:25]([NH:24][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:30]3)[CH:47]=1

참가 물질

4

반응물 2

HCID 2724995Triethyl(methoxycarbonylsulfamoyl)aminiumHCID 86762658(4aR,6R,8aS)-2-(benzoylamino)-8a-(5-bromo-2-fluorophenyl)-N-(1-oxopropan-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazine-6-carboxamide

생성물 1

HCID 86762659N-[(4aR,6R,8aS)-8a-(5-bromo-2-fluorophenyl)-6-(4-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Methyl N-(triethylammoniumsulfonyl)carbamate (Burgess reagent) (0.811 g, 3.40 mmol) was added to a solution of (4aR,6R,8aS)-2-(benzoylamino)-8a-(5-bromo-2-fluorophenyl)-N-(1-oxopropan-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazine-6-carboxamide (C39) (0.747 g, 1.36 mmol) in toluene (34 mL). The resulting solution was stirred at room temperature for 10 minutes, followed by heating to 65° C. for 16 hours. The reaction mixture was concentrated under reduced pressure. Purification via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) afforded the product as a yellow oily residue. Yield: 417 mg, 58%. LCMS m/z 532.1 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 8.17 (br s, 2H), 7.36-7.54 (m, 5H), 7.36 (q, J=1.2 Hz, 1H), 7.01-7.06 (m, 1H), 4.83 (dd, J=12.0, 2.4 Hz, 1H), 4.31 (dd, J=11.9, 1.6 Hz, 1H), 3.07 (dd, J=13.0, 3.8 Hz, 1H), 2.70 (m, 1H), 2.58-2.54 (m, 1H), 2.17 (d, J=1.7 Hz, 3H), 2.08-2.14 (m, 1H).

후처리

  1. temperatureby heating to 65° C. for 16 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customPurification via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane)
  4. customafforded the product as a yellow oily residue

출처 및 근거

ORD 기록
ord-847b78a23d03445ebae0b555c7e1f0f7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822456B2

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