Hydrochloric Acid → HCID 22873065, compound

HRID 1781573Notes

Reaction equation

HRID 1781573 reaction equation
[Br:1][C@@H:2]1[C@:6](C(=O)C)([OH:7])[C@@H:5]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[O:4][C@H:3]1[N:16]1[CH:23]=[C:22]([CH3:24])[C:20](=[O:21])[NH:19][C:17]1=[O:18].O.NN.Cl>O.C(#N)C>[Br:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[O:4][C@H:3]1[N:16]1[CH:23]=[C:22]([CH3:24])[C:20](=[O:21])[NH:19][C:17]1=[O:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 67581565HCID 67581565, compound

Product 1

HCID 22873065HCID 22873065, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

400 ml of acetonitrile and 2.16 g (3 equivalents) of water were added to 16.2 g (40.0 mmol) of 2'-deoxy-2'-bromo-3',5'-O-diacetyl-5-methyluridine, and the mixture was stirred. The resulting solution was cooled to 0° C., 6.01 g (3 equivalents) of hydrazine monohydrate were added thereto, and the mixture was reacted for 20 hours at that temperature. 100 ml of water were added to the reaction mixture, which was then neutralized to a pH of 6.8 by adding 6 N-hydrochloric acid thereto. The acetonitrile layer was separated, washed with saturated saline solution, dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 13.5 g of 2'-deoxy-2'-bromo-5'-O-acetyl-5-methyluridine. Its purity was 81.8%. Its yield was 76.0%.

Workup

  1. customthe mixture was reacted for 20 hours at that temperature
  2. customThe acetonitrile layer was separated
  3. washwashed with saturated saline solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1599ec65fdd54d67a7b447137a9c1a30
Source dataset
uspto-grants-1997_05
Patent number
US05633366

Reaction notes

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