Hydrochloric Acid → HCID 10900246, compound

HRID 249055Notes

Reaction equation

HRID 249055 reaction equation
CS(O[C@@H:6]1[C@@H:10]([CH2:11][O:12]S(C)(=O)=O)[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)(=O)=O.[OH-].[Na+].Cl>O>[C@@H:8]1([N:17]2[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[O:9][C@@H:10]2[CH2:11][O:12][C@@H:6]2[CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 105729323',5'-DI-O-Mesylthymidine

Product 1

HCID 10900246HCID 10900246, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3',5'-Di-O-(methanesulfonyl)thymidine (248 g, 0.62M) was added in portions to a stirred solution of sodium hydroxide (74.7 g, 1.87M) in water (1.6 L). On addition 3 the reaction mixture became a yellow-orange solution. This stirred solution was then heated to reflux for 2 hr. Once the reaction mixture had cooled to room temperature, 6N hydrochloric acid (100 mL) was added. The reaction mixture was concentrated in vacuo by removing 1.3 L of water. The resulting slurry was cooled in an ice bath for 2 hr. The solid was then filtered and washed sparingly with ice water, and then vacuum dried to constant weight (103.7 g, 74%). The product 3, mp 188°-190° C. (lit. 190°-193° C.) was used without further purification. 1H NMR (360 MHz, d6 -DMSO) 11.35 (s, 1H, NH), 8.01 (s, 1H, H-6), 6.49 (q, 1H, H-1 '), 5.47 (m, 1H, H-3'), 4.88 and 4.67 (m, 2H, H-5'), 4.22 (d, 1H, H-4'), 2.47 (m, 2H, H-2') 1.77 (S, 3H, CH3). 13C NMR (75 MHz, d6 -DMSO) 163.64 (C2), 151.10 (C4), 136.57 (C6), 109.62 (C5), 88.29 (C4'), 86.85 (C1'), 79.83 (C3'), 75.14 (C5'), 37.17 (C2'), 12.33 (CH3). Analysis (C10H12N2O4) C, H, N.

Workup

  1. additionOn addition 3 the reaction mixture
  2. temperatureThis stirred solution was then heated
  3. temperatureto reflux for 2 hr
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customby removing 1.3 L of water
  6. temperatureThe resulting slurry was cooled in an ice bath for 2 hr
  7. filtrationThe solid was then filtered
  8. washwashed sparingly with ice water
  9. customvacuum dried to constant weight (103.7 g, 74%)
  10. customThe product 3, mp 188°-190° C. (lit. 190°-193° C.) was used without further purification

Sources & evidence

ORD record
ord-071fc750a5e8438a9483db44246f8cc5
Source dataset
uspto-grants-1993_05
Patent number
US05212294

Reaction notes

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