Hydrochloric Acid → Ethyl-7-{[4-(1-Hydroxy-3-phenyl-propyl)-benzyl]-methanesulfonyl-amino}-heptanoate

HRID 480271ノート

反応式

HRID 480271 の反応式
[CH:1]([C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]([S:20]([CH3:23])(=[O:22])=[O:21])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=1)=[O:2].[CH2:26]([Mg]Cl)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O.Cl>C(Cl)Cl>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([CH:1]([OH:2])[CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:25][CH:24]=1)[S:20]([CH3:23])(=[O:22])=[O:21])[CH3:19]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 22246810Ethyl 7-[(4-formyl-benzyl)-methanesulfonyl-amino]-heptanoateHCID 178418865HCID 178418865、化合物

生成物 1

HCID 22246896Ethyl-7-{[4-(1-Hydroxy-3-phenyl-propyl)-benzyl]-methanesulfonyl-amino}-heptanoate収率 15.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of ethyl 7-[(4-formyl-benzyl)-methanesulfonyl-amino]-heptanoate (200 mg, 0.54 mmol) in CH2Cl2 (2.5 mL) was cooled to 0° C. Phenethylmagnesium chloride (0.6 mL, 1M in THF, 0.6 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 24 h. Water and HCl (1N) were added and the aqueous solution was extracted with CH2Cl2. The organic solution was washed with water (1×) followed by brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography (10% EtOAc/hex to 40% EtOAc/hex) to afford the title compound of Step A (40 mg). 1H NMR (400 MHz, CDCl3) δ 6 7.95 (d, 1H), 7.45 (d, 1H), 7.13-7.40 (m, 7H), 4.654.73 (m, 1H), 4.324.46 (m, 2H), 4.11 (q, 2H), 3.25-3.35 (m, 1H), 3.00-3.22 (m, 2H), 2.83 (s, 3H), 2.60-2.81 (m, 1H), 1.96-2.34 (m, 4H), 1.15-1.70 (m, 12H); MS 493 (M+18).

後処理

  1. extractionthe aqueous solution was extracted with CH2Cl2
  2. washThe organic solution was washed with water (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography (10% EtOAc/hex to 40% EtOAc/hex)

出典と根拠

ORDレコード
ord-813ab8dee6fd4027972382315620c122
出典データセット
uspto-grants-2003_11
特許番号
US06649657B2

反応ノート

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