Aniline → (6S)-allyl-(4-oxo-6-phenylcarbamoyl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl)-carbamic Acid Benzyl Ester

HRID 10968

反応式

HRID 10968 の反応式
[CH2:1]([N:4]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C:5]1[C:10](=[O:11])[N:9]2[C@H:12]([C:15]([OH:17])=O)[CH2:13][CH2:14][C:8]2=[N:7][CH:6]=1)[CH:2]=[CH2:3].[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1C=NC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+].CCN=C=NCCCN(C)C>CCOC(C)=O.C(Cl)Cl.CN(C=O)C>[CH2:21]([O:20][C:18](=[O:19])[N:4]([CH2:1][CH:2]=[CH2:3])[C:5]1[C:10](=[O:11])[N:9]2[C@H:12]([C:15](=[O:17])[NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:13][CH2:14][C:8]2=[N:7][CH:6]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

8

反応物 5

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 58681925(6S)-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid

生成物 1

HCID 69600602(6S)-allyl-(4-oxo-6-phenylcarbamoyl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl)-carbamic Acid Benzyl Ester

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 18a (5.50 g, 14.89 mmol) and aniline (1.93 mL, 22.3 mmol) in 75 mL 5:1 CH2Cl2/DMF at 0° C., was added HOAT (2.23 g, 16.4 mmol), NaHCO3 (2.50 g, 29.8 mmol), and EDCI (4.00 g, 20.8 mmol). The mixture was stirred and allowed to warm to rt over 72 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 (80 to 90% EtOAc/hexanes) to afford 3.825 g (58%, 2 steps) of 18b as an off-white solid.

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 (80 to 90% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-3893d05062934c729de80100e116eee3
出典データセット
uspto-grants-2006_08
特許番号
US07094783B2

関連ノート

読み込み中…