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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
ノート
印刷プレビュー

反応式

HRID 10991 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

HCID 145857219
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
収率 20.8%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-384eab5d229c455fb8dd63aeadcf8621
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07094783B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート