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

HRID 1696982

Reaction equation

HRID 1696982 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(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+).

Workup

  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

Sources & evidence

ORD record
ord-ea25eb94c75141c08db1079dd524468d
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Linked notes

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