Diethyl Pyrocarbonate → HCID 178495709、化合物

HRID 550306ノート

反応式

HRID 550306 の反応式
Cl.[CH3:2][O:3][CH2:4][C@H:5]1[C@H:14]2[CH2:15][CH2:16][N:17]([C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH2:26])=[O:19])[C@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1.C(N(CC)CC)C.[NH:34]1[C:38]2[CH:39]=[CH:40][C:41]([C:43](O)=[O:44])=[CH:42][C:37]=2[N:36]=[N:35]1.CCOC(OC(OCC)=O)=O>C1COCC1.O>[CH3:2][O:3][CH2:4][C@H:5]1[C@H:14]2[CH2:15][CH2:16][N:17]([C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH:26][C:43]([C:41]3[CH:40]=[CH:39][C:38]4[NH:34][N:35]=[N:36][C:37]=4[CH:42]=3)=[O:44])=[O:19])[C@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1

参加物

7

反応物 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 67150575(1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochlorideHCID 178524184HCID 178524184、化合物

生成物 1

HCID 178495709HCID 178495709、化合物収率 80%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution (5 ml) of (1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride (200 mg, 0.480 mmol) in THF were added triethylamine (0.199 ml, 1.44 mmol), 1H-1,2,3-benzotriazole-5-carboxylic acid (78.3 mg, 0.480 mmol) and DEPC (0.079 ml, 0.528 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4, and concentrated under reduced pressure. The obtained residue was subjected to column chromatography using silica gel and eluted with hexane:ethyl acetate (1:1-1:9) to give the title compound (187 mg, 80%) as an amorphous form.

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. washeluted with hexane:ethyl acetate (1:1-1:9)

出典と根拠

ORDレコード
ord-d6ba24cb92524e08b2a9b01469e564da
出典データセット
uspto-grants-2011_05
特許番号
US07943770B2

反応ノート

読み込み中…