N,N-Dimethylaniline → Tert-butyl 3-(4-((2'-((dimethylamino)carbonyl)biphenyl-3-yl)methoxy)phenyl)propanoate

HRID 2422299ノート

反応式

HRID 2422299 の反応式
[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]1[CH:32]=[CH:31][C:13]([O:14][CH2:15][C:16]2[CH:17]=[C:18]([C:22]3[C:23]([C:28](O)=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:33][N:34](C)[C:35]1C=CC=CC=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(OCC)(=O)C.C(=O)([O-])O.[Na+].CN(C)C=O>[CH3:33][N:34]([CH3:35])[C:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][O:14][C:13]2[CH:31]=[CH:32][C:10]([CH2:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:11][CH:12]=2)[CH:17]=1)=[O:29]

参加物

8

反応物 4

HCID 949N,N-DimethylanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 575418463'-[4-(2-Tert-butoxycarbonylethyl)phenoxymethyl]biphenyl-2-carboxylic acid

生成物 1

HCID 23083025Tert-butyl 3-(4-((2'-((dimethylamino)carbonyl)biphenyl-3-yl)methoxy)phenyl)propanoate

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a mixture of 3′-[4-(2-tert-butoxycarbonylethyl)phenoxymethyl]biphenyl-2-carboxylic acid (0.24 g, 0.56 mmol), dimethylaniline (2M tetrahydrofuran solution, 0.42 mL, 0.84 mmol), 1-hydroxybenzotriazole monohydrate (0.13 g, 0.84 mmol) and N,N-dimethylformamide (6.0 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.16 g, 0.84 mmol) at room temperature with stirring, and the mixture was stirred at the same temperature for 12 hrs. The reaction mixture was diluted with ethyl acetate, saturated aqueous sodium hydrogen carbonate, washed successively with 5% aqueous potassium hydrogensulfate solution and saturated brine, dried (anhydrous magnesium sulfate), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-1/2) to give tert-butyl 3-(4-((2′-((dimethylamino)carbonyl)biphenyl-3-yl)methoxy)phenyl)propanoate as a colorless oil. This compound was dissolved in trifluoroacetic acid (2 mL), and the mixture was stirred at room temperature for 1 hr, and concentrated under reduced pressure. The residue was purified by preparative HPLC (gradient cycle A) to give the title compound (58 mg, yield 26%) as colorless crystals. MS (APCI−): 402 (M−H).

後処理

  1. stirringthe mixture was stirred at the same temperature for 12 hrs
  2. washwashed successively with 5% aqueous potassium hydrogensulfate solution and saturated brine
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-1/2)

出典と根拠

ORDレコード
ord-300ac28a1de34807ba6fd9670e21b910
出典データセット
uspto-grants-2011_06
特許番号
US07960369B2

反応ノート

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