Ethyl Acetate → 3-Amino-9-chloro-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine

HRID 459896ノート

反応式

HRID 459896 の反応式
[N:1]([CH:4]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]2[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:7]=2[N:6]([CH2:22][C:23]([F:26])([F:25])[F:24])[C:5]1=[O:27])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1.O.[Cl-].[Na+].O>[NH2:1][CH:4]1[N:10]=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:7]=2[N:6]([CH2:22][C:23]([F:26])([F:24])[F:25])[C:5]1=[O:27]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 184442503-Azido-9-chloro-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine

生成物 1

HCID 184442493-Amino-9-chloro-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine収率 51.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of 3-azido-9-chloro-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine (0.320 g, 0.812 mmol) and triphenylphosphine (0.426 g, 1.62 mmol) in tetrahydrofuran (13 mL) and water (1.5 mL) was stirred at room temperature for 48 h. Workup with ethyl acetate and saturated sodium bicarbonate, followed by saturated brine and drying over sodium sulfate gave the product. The crude product was purified by chromatography (silica gel, 0–5% methanol in methylene chloride gradient elution), giving the title compound (0.155 g). 1H NMR (500 MHz, CDCl3) δ 7.65 (d, J=8 Hz, 2H), 7.49 (tt, J=2,7 Hz, 1H), 7.42 (t, J=8 Hz, 2H), 7.32 (t, J=8 Hz, 1H), 7.26 (d, J=7 Hz, 1H), 5, 22 (m, 1H), 4.56 (s, 1H), 4.30 (m, 1H), 2.15 (br s, 2H).

後処理

  1. dry with materialdrying over sodium sulfate
  2. customgave the product
  3. customThe crude product was purified by chromatography (silica gel, 0–5% methanol in methylene chloride gradient elution)

出典と根拠

ORDレコード
ord-f41423c6ae02483f81a2d839fcdb4be1
出典データセット
uspto-grants-2007_03
特許番号
US07196079B2

反応ノート

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