1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → benzyl N-[(6S,8R)-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-8-prop-2-enyl-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate

HRID 10991

반응식

HRID 10991 반응식
[CH2:1]([C@H:4]1[C:8]2=[N:9][CH:10]=[C:11]([N:14]([CH2:25][CH:26]=[CH2:27])[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[C:12](=[O:13])[N:7]2[C@H:6]([C:28](O)=[O:29])[CH2:5]1)[CH:2]=[CH2:3].Cl.[CH2:32]([O:39][C:40](=[O:52])[NH:41][C:42]([C:44]1[CH:49]=[CH:48][C:47]([CH2:50][NH2:51])=[CH:46][CH:45]=1)=[NH:43])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1C=NC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[CH2:25]([N:14]([C:11]1[C:12](=[O:13])[N:7]2[C@H:6]([C:28](=[O:29])[NH:51][CH2:50][C:47]3[CH:46]=[CH:45][C:44]([C:42]([NH:41][C:40]([O:39][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:52])=[NH:43])=[CH:49][CH:48]=3)[CH2:5][C@@H:4]([CH2:1][CH:2]=[CH2:3])[C:8]2=[N:9][CH:10]=1)[C:15](=[O:16])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:26]=[CH2:27]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 57444828(6S,8R)-8-allyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic AcidHCID 145832047Benzyl ((4-(aminomethyl)phenyl)(imino)methyl)carbamate hydrochloride

생성물 1

HCID 145857219benzyl N-[(6S,8R)-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-8-prop-2-enyl-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate수율 20.8%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

To a solution of 28d (172 mg, 0.420 mmol) and [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride (180 mg, 0.504 mmol) in 3.6 mL CH2Cl2/DMF (5:1) at 0° C., was added HOAT (113 mg, 0.588 mmol), NaHCO3 (141 mg, 1.68 mmol), and EDCI (113 mg, 0.588 mmol). The mixture was allowed to warm to rt and stir for 64 h. The reaction was diluted with EtOAc and the organic phase was washed with H2O, 1N HCl, H2O, and brine. The organic phase was dried (Na2SO4) and concentrated. The residue obtained was purified by flash chromatography (75% EtOAc/hexanes) to afford 59 mg of intermediate 28e.

후처리

  1. washthe organic phase was washed with H2O, 1N HCl, H2O, and brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue obtained
  5. customwas purified by flash chromatography (75% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-384eab5d229c455fb8dd63aeadcf8621
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094783B2

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