Water → (2R)-2-amino-N-[5-{3-[(2-chloropyridin-4-yl)methyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl}-2-(trifluoromethoxy)phenyl]-2-phenylacetamide

HRID 546571

反応式

HRID 546571 の反応式
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2N=N1.[CH2:23]([N:25](CC)CC)[CH3:24].[NH2:30][C:31]1[CH:32]=[C:33]([N:42]2[C:46](=[O:47])[C:45]([CH3:49])([CH3:48])[N:44]([CH2:50][C:51]3[CH:56]=[CH:55][N:54]=[C:53]([Cl:57])[CH:52]=3)[C:43]2=[O:58])[CH:34]=[CH:35][C:36]=1[O:37][C:38]([F:41])([F:40])[F:39].[OH2:59]>CN(C)C=O>[NH2:25][C@H:23]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:24]([NH:30][C:31]1[CH:32]=[C:33]([N:42]2[C:46](=[O:47])[C:45]([CH3:49])([CH3:48])[N:44]([CH2:50][C:51]3[CH:56]=[CH:55][N:54]=[C:53]([Cl:57])[CH:52]=3)[C:43]2=[O:58])[CH:34]=[CH:35][C:36]=1[O:37][C:38]([F:39])([F:40])[F:41])=[O:59]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 576260063-[3-Amino-4-(trifluoromethoxy)phenyl]-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione

生成物 1

HCID 86629090(2R)-2-amino-N-[5-{3-[(2-chloropyridin-4-yl)methyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl}-2-(trifluoromethoxy)phenyl]-2-phenylacetamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a solution of 0.6 g of D-N-Boc-phenylglycine in 12 mL of dimethylformamide is added 0.74 g or O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU). After stirring for 5 minutes, 0.837 mL of triethylamine and 0.86 g of 3-[3-amino-4-(trifluoromethoxy)phenyl]-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione obtained in stage c) below are successively added. The reaction mixture is heated at 70° C. for 15 hours and then poured into 100 mL of water. The aqueous phase is extracted with three times 70 mL of ethyl acetate and the combined organic phases are washed with 50 mL of saturated sodium chloride solution, dried over magnesium sulphate, filtered and evaporated. The residue is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and ethyl acetate (70/30 by volume) to give 220 mg of (2R)-2-amino-N-[5-{3-[(2-chloropyridin-4-yl)methyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl}-2-(trifluoromethoxy)phenyl]-2-phenylacetamide, the characteristics of which are as follows:

後処理

  1. extractionThe aqueous phase is extracted with three times 70 mL of ethyl acetate
  2. washthe combined organic phases are washed with 50 mL of saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by chromatography on a column of silica
  7. washeluting with a mixture of dichloromethane and ethyl acetate (70/30 by volume)

出典と根拠

ORDレコード
ord-1cdef8915ae345ef922b3be0fca5f887
出典データセット
uspto-grants-2011_05
特許番号
US07935819B2

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