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 29194ノート

反応式

HRID 29194 の反応式
[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

参加物

5

反応物 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

生成物 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]carbamate収率 129.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-449bb7a6332243be827f8cf40e29a827
出典データセット
uspto-grants-2008_09
特許番号
US07419967B2

反応ノート

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