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

반응식

HRID 546571 반응식
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]

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

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:

후처리

  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)

출처 및 근거

ORD 기록
ord-1cdef8915ae345ef922b3be0fca5f887
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935819B2

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