2-(Tert-butoxycarbonylmethyl-amino)-propionic acid methyl ester → {3-[2-Fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5-methyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid tert-butyl ester

HRID 600271

반응식

HRID 600271 반응식
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][N:8]=2)=[CH:4][C:3]=1[N:20]=[C:21]=[O:22].C[O:24][C:25](=O)[CH:26]([NH:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH3:27]>C(Cl)Cl>[C:33]([O:32][C:30](=[O:31])[CH2:29][N:28]1[CH:26]([CH3:27])[C:25](=[O:24])[N:20]([C:3]2[CH:4]=[C:5]([CH2:6][C:7]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:10](=[O:17])[NH:9][N:8]=3)[CH:18]=[CH:19][C:2]=2[F:1])[C:21]1=[O:22])([CH3:35])([CH3:34])[CH3:36]

참가 물질

4

반응물 2

HCID 216437342-(Tert-butoxycarbonylmethyl-amino)-propionic acid methyl esterHCID 598565454-(4-Fluoro-3-isocyanato-benzyl)-2H-phthalazin-1-one

생성물 1

HCID 68910449{3-[2-Fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5-methyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid tert-butyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 4-(3-isocyanato-benzyl)-2H-phthalazin-1-one (2)(3.12 mmol) in dry DCM (80 ml) in the presence of activated 4 Å molecular sieves (ca 5 g) was added 2-(tert-butoxycarbonylmethyl-amino)-propionic acid methyl ester (33A)(1.07 g, 4.7 mmol). The reaction was then stirred for 48 hours at ambient temperature. HPLC analysis showed there to a mixture of cyclised and uncyclised ureas 1:1 ratio. The mixture was filtered and concentrated in vacuo. The crude oil was then subjected to flash chromatography eluent: 1:1 hexane ethyl acetate, Rf=0.09. Single peak in LC-MS analysis, (1.3 g, 95% purity) and required no further purification; m/z (LC-MS, ESP), RT=3.66 mins (M+H) 481—compound cyclised on column

후처리

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customno further purification

출처 및 근거

ORD 기록
ord-aad5ee53553d4a7fbbf55288cd14e8f9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902193B2

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