Hydrochloric Acid → 4-[[(1R)-3-(4-morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-nitroBenzenesulfonamide

HRID 1771204ノート

反応式

HRID 1771204 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([C:7](=O)[CH2:8][C@@H:9]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][C:20]=2[N+:29]([O-:31])=[O:30])[CH2:10][S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3][CH2:2]1.B.C1COCC1.Cl.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.CO>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C@@H:9]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:26])=[O:27])=[CH:21][C:20]=2[N+:29]([O-:31])=[O:30])[CH2:10][S:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 11591105(R)-4-(4-morpholino-4-oxo-1-(phenylthio)butan-2-ylamino)-3-nitrobenzenesulfonamide2 回

生成物 1

HCID 117054054-[[(1R)-3-(4-morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-nitroBenzenesulfonamide収率 80%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(R)-4-(4-Morpholino-4-oxo-1-(phenylthio)butan-2-ylamino)-3-nitrobenzenesulfonamide (INTERMEDIATE 73, 523.6 mg, 1.09 mmol) was dissolved under a nitrogen atmosphere in a solution of borane-THF complex (1M in THF; 2.4 ml, 2.4 mmol) and the resulting solution was stirred at room temperature overnight. The flask was opened to atmosphere and cautiously treated with MeOH (1.20 ml) followed by concentrated HCl (0.48 ml). The resulting mixture was heated at reflux for 3 hours and was then allowed to cool to room temperature. The pH of the mixture was adjusted to approximately 10 by the addition of aqueous solution of Na2CO3 (4 M) resulting in a precipitate. The mixture was dissolved in EtOAc (75 ml) and washed with water (40 ml), brine (40 ml), and dried (Na2SO4). Evaporation of the volatiles under reduced pressure afforded a concentrate, which was purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% EtOAc/hexanes) to provide the title product (406.6 mg, yield: 80%).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureto cool to room temperature
  4. customresulting in a precipitate
  5. washwashed with water (40 ml), brine (40 ml)
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the volatiles under reduced pressure
  8. customafforded a concentrate, which
  9. customwas purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-371bc7e7aa3c42fea67d15028a0d6bb3
出典データセット
uspto-grants-2016_02
特許番号
US09248140B2

反応ノート

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