Hydrochloric Acid → Racivir

HRID 323908Notes

Reaction equation

HRID 323908 reaction equation
[CH2:1]1[S:5][C@H:4]([CH2:6][OH:7])[O:3][C@@H:2]1[N:8]1[C:13](=[O:14])[N:12]=[C:11]([NH2:15])[C:10]([F:16])=[CH:9]1.Cl>CO.O1CCOCC1>[NH2:15][C:11]1[C:10]([F:16])=[CH:9][N:8]([CH:2]2[O:3][CH:4]([CH2:6][OH:7])[S:5][CH2:1]2)[C:13](=[O:14])[N:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 60877Emtricitabine

Product 1

HCID 9837769Racivir

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (−)-FTC [32(2R, β/α)](60:40 of a β:α anomer mixture, 3.0 g) was dissolved in methanol (30 ml), cooled to 0° C., and treated with a 4.0 M solution of HCl in 1,4-dioxane (3.3 ml [1.1x]). The solution was stirred for 20 minutes, and subsequently concentrated to dryness affording an off-white solid.

Workup

  1. concentrationsubsequently concentrated to dryness
  2. customaffording an off-white solid

Sources & evidence

ORD record
ord-27217238c5624324837a1077f9a5e528
Source dataset
uspto-grants-2001_04
Patent number
US06215004B1

Reaction notes

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