Pyridine → Carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester

HRID 1696982

반응식

HRID 1696982 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([OH:16])[CH:13]=[CH:12]2)=[C:4]([Cl:17])[N:3]=1.N1C=CC=CC=1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26]>C1COCC1>[CH2:28]([O:27][C:25](=[O:26])[O:16][C@H:14]1[CH2:15][C@@H:11]([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([Cl:1])=[N:3][C:4]=3[Cl:17])[CH:12]=[CH:13]1)[CH3:29]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 10378467(1S,4R)-4-(2,6-Dichloro-9H-purin-9-yl)cyclopent-2-en-1-ol

생성물 1

HCID 58025019Carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(1S,4R)-4-(2,6-Dichloro-purin-9-yl)-cyclopent-2-enol (9.5 g, 35.05 mmol) is placed in an oven-dried flask under an atmosphere of argon. Dry THF (200 mL) is added followed by dry pyridine (5.54 g, 70.1 mmol). Ethyl chloroformate (15.21 g, 140.2 mmol) is added slowly so that the temperature does not rise above 40-C and the reaction mixture is stirred at room temperature. The reaction is shown to be complete by LCMS after 1 hour. The solvent is removed in vacuo and the residue is partitioned between dichloromethane (200 mL) and water (200 mL). The organic layer is washed with water (150 ml) and brine (150 ml), dried over MgSO4, filtered and the solvent is removed in vacuo. The title compound is obtained after crystallisation from methanol. 1H nmr (CDCl3, 400 MHz); 8.20(s, 1H), 6.45(m, 1H), 6.25(m, 1H), 5.75(m, 1H), 5.70(m, 1H), 4.25(q, 2H), 3.20(m, 1H), 2.05(m, 1H), 1.35(t, 3H), MS (E+) m/e 343 (MH+).

후처리

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between dichloromethane (200 mL) and water (200 mL)
  3. washThe organic layer is washed with water (150 ml) and brine (150 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

출처 및 근거

ORD 기록
ord-ea25eb94c75141c08db1079dd524468d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163754B2

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