Potassium Carbonate → (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-1-benzyl-3-((cyclopentyloxy)[3-(2-morpholino-2-oxoethoxy)phenyl]sulfonylamino)-2-hydroxypropyl]carbamate

HRID 29194노트

반응식

HRID 29194 반응식
[CH2:1]([C@H:8]([NH:29][C:30](=[O:40])[O:31][C@@H:32]1[C@H:39]2[C@H:35]([O:36][CH2:37][CH2:38]2)[O:34][CH2:33]1)[C@@H:9]([OH:28])[CH:10]([NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1)(=[O:20])=[O:19])OC1CCCC1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:42][C:43]([N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1)=[O:44].[C:51](=[O:54])([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([C@H:8]([NH:29][C:30](=[O:40])[O:31][C@@H:32]1[C@H:39]2[C@H:35]([O:36][CH2:37][CH2:38]2)[O:34][CH2:33]1)[C@H:9]([OH:28])[CH2:10][N:17]([O:54][CH:51]1[CH2:3][CH2:2][CH2:1][CH2:8]1)[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:42][C:43]([N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)=[O:44])[CH:22]=1)(=[O:19])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 139968762-Bromo-1-(morpholin-4-yl)ethan-1-oneHCID 69223281(3R,3aS,6aR)hexahydrofuro [2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(3-hydroxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

생성물 1

HCID 21356316(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-1-benzyl-3-((cyclopentyloxy)[3-(2-morpholino-2-oxoethoxy)phenyl]sulfonylamino)-2-hydroxypropyl]carbamate수율 129.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(3-hydroxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate (0.09 mmol, 50 mg) was combined with 2-bromo-1-morpholino-1-ethanone (0.09 mmol, 18 mg) and potassium carbonate (0.26 mmol, 36 mg), and stirred in anhydrous DMF (1 mL) under nitrogen for 15 hours at room temperature. The reaction was concentrated to a residue, dissolved in ethyl acetate, washed in distilled water and brine, and dried over magnesium sulfate. The dried solution was then concentrated and purified by silica gel flash chromatography (1:1 hexanes/ethyl acetate) to provide 41 mg (67%) of a white solid. Rf=0.1 (1:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.47 (2H,m), 7.38 (1H,m), 7.32-7.14 (7H,m), 5.64 (1H,s), 5.03(2H,m), 4.91-4.76 (1H,m), 4.78 (2H,s), 3.98-3.89 (2H,m), 3.89-3.77 (2H,m), 3.74-3.63 (8H,m), 3.63-3.52 (2H,m), 3.15 (1H,br.s), 3.08-2.98 (2H,m), 2.98-2.84 (3H,m), 2.84-2.74 (1H,m), 1.89-1.71 (4H,m), 1.71-1.49 (4H,m). MS (ESI): M+H=704.

후처리

  1. concentrationThe reaction was concentrated to a residue
  2. dissolutiondissolved in ethyl acetate
  3. washwashed in distilled water
  4. dry with materialbrine, and dried over magnesium sulfate
  5. concentrationThe dried solution was then concentrated
  6. custompurified by silica gel flash chromatography (1:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-449bb7a6332243be827f8cf40e29a827
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419967B2

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