Hydrochloric Acid → HCID 54435225, compound

HRID 1007592Notes

Reaction equation

HRID 1007592 reaction equation
C([O:4][C@@H:5]1[C@:9]([CH:18]=[CH2:19])([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:8]([CH2:20][O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:7][C@H:6]1[N:29]1[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]1=[O:31])(=O)C.C[O-].[Na+].Cl>CO>[CH2:11]([O:10][C@:9]1([CH:18]=[CH2:19])[C@@H:8]([CH2:20][O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:7][C@@H:6]([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[C@@H:5]1[OH:4])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 15332428HCID 15332428, compound

Product 1

HCID 54435225HCID 54435225, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of nucleoside 23 (3.90 g, 7.7 mmol) in anhydrous methanol (40 cm3) was added sodium methoxide (0.83 g, 15.4 mmol). The mixture was stirred at room temperature for 42 h and then neutralised with dilute aqueous hydrochloric acid. The mixture was extracted with dichloromethane (2×150 cm3), and the combined extract was washed with saturated aqueous sodium hydrogencarbonate (3×100 cm3) and dried (Na2SO4). The solvent was removed under reduced pressure to give nucleoside 24 as a white foam (3.48 g, 97%). δH (CDCl3) 8.89 (1H, br s, NH), 7.60 (1H, d, J 0.9, 6-H), 7.36-7.26 (10H, m, Bn), 6.23 (1H, d, J 7.8, 1′-H), 5.98 (1H, dd, J 11.2, 17.7, 1″-H), 5.66 (1H, d, J 17.7, 2″-Ha), 5.55 (1H, d, J 11.5, 2″-Hb), 4.75-4.37 (6H, m, 2′-H, 4′-H, Bn), 3.84 (1H, dd, J 2.7, 10.8, 5′-Ha), 3.58 (1H, d, J 11.2, 5′-Hb), 3.23 (1H, d, J 10.6, 2′-OH), 1.50 (3H, s, CH3). δC (CDCl3) 163.7 (C-4), 151 3 (C-2), 138.0, 136.9 (Bn), 136.0 (C-6), 131.2 (C-1″), 128.8, 128.6, 128.3, 127.8, 127.7, 127.3 (Bn), 120.7 (C-2″), 111.3 (C-5), 87.3 (C-1′), 84.6 (C-3′), 81.4 (C-4′), 78.0 (C-2′), 73.7 (C-5′), 70.0, 66.4 (Bn), 11.8 (CH3). Found: C, 66.8; H, 6.2; N, 5.9. C26H28N2O6 requires C, 67.2; H, 6.1: N, 6.0%.

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×150 cm3)
  2. extractionthe combined extract
  3. washwas washed with saturated aqueous sodium hydrogencarbonate (3×100 cm3)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-359c0bddfcc547bebdc32b8876deaa70
Source dataset
uspto-grants-2004_09
Patent number
US06794499B2

Reaction notes

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