Water → HCID 18639108, compound

HRID 1649882Notes

Reaction equation

HRID 1649882 reaction equation
S(O[C@H:6]1[C@@H:10]([CH2:11][O:12][C:13]([O:15][CH3:16])=[O:14])[O:9][C@@H:8]([N:17]2[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:7]1)(C)(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+].O>CN(C)C=O>[N:26]([C@@H:6]1[C@@H:10]([CH2:11][O:12][C:13]([O:15][CH3:16])=[O:14])[O:9][C@@H:8]([N:17]2[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:7]1)=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 14697458HCID 14697458, compound

Product 1

HCID 18639108HCID 18639108, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-[2-deoxy-3-O-mesyl-5-O-methoxycarbonyl-β-D-threopentofuranosyl]-thymine (5.0 g, 13.2 mmoles) from Example A13 and sodium azide (1.07 g, 16.5 mmoles) in dimethylformamide (40 mL) was heated at 85°-90° C. for 4 h. The suspension was cooled to ambient temperature poured into 300 mL of water and the aqueous solution extracted with 3×100 mL portions of ethyl acetate. The combined organic extracts were washed with 2×100 mL portions of water and concentrated by rotary evaporation affording 3.88 g (90.2%) of 3'-azido-3'-deoxy-5'-O-(methoxycarbonyl)thymidine as a colorless oil: 1H NMR (CDCl3) δ1.91 (d, J=1.15 Hz, 3H, C-5-CH3), 2.30-2.49 (m, 2H, C-2'H), 3.83 (s, 3H, CO2CH3), 3.97-4.44 (m, 4H, C-3'H, C-4'H and C-5'H), 6.21 (t, J=6.26 Hz, 1H, C-1'H), 7.29 (q, J=1.15 Hz, 1H, C-6H) and 8.75 (broad, 1H, NH); 13C NMR (CDCl3) δ12.42, 37.57, 55.28, 60.04, 66.39, 81.56, 84.94, 111.38, 135.28, 150.45, 155.18 and 164.03; TLC, Rf =0.78, silica gel, CHCl3 :CH3OH/90:10.

Workup

  1. temperaturewas heated at 85°-90° C. for 4 h
  2. extractionthe aqueous solution extracted with 3×100 mL portions of ethyl acetate
  3. washThe combined organic extracts were washed with 2×100 mL portions of water
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-d4d1adadd604461c8bdeb44caa26b753
Source dataset
uspto-grants-1990_05
Patent number
US04921950

Reaction notes

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