Emtricitabine → HCID 131725250, compound

HRID 489711Notes

Reaction equation

HRID 489711 reaction equation
[C:1]([O-:6])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:7]1[S:11][C@@H:10]([CH2:12][OH:13])[O:9][C@H:8]1[N:14]1[C:19](=[O:20])[N:18]=[C:17]([NH2:21])[C:16]([F:22])=[CH:15]1.C1S[C@H](CO)O[C@@H]1N1C(=O)N=C(N)C(F)=C1>P([O-])([O-])([O-])=O.C(O)(C)C>[CH2:7]1[S:11][C@H:10]([CH2:12][OH:13])[O:9][C@@H:8]1[N:14]1[C:19](=[O:20])[N:18]=[C:17]([NH2:21])[C:16]([F:22])=[CH:15]1.[C:1]([O-:6])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 60877Emtricitabine2×HCID 104775ButyrateHCID 454858(+)-2′-Deoxy-3′-thia-5-fluorocytidine2×

Product 1

HCID 131725250HCID 131725250, compound

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 3776IsopropanolSolvent

Procedure

The following example illustrates the state of the art using high amounts of enzyme catalysts in a of homogeneous system. To a solution of 1 ml of Altus PLE solution 650 units/ml from Altus Biologics, Inc. in 39 ml of 0.3 M phosphate buffer (pH 7.5) was added 10 ml of 10% FTC butyrate in isopropanol. The resulting mixture was stirred 24˜26° C. and the reaction progress was monitored by HPLC. The conversion reached 51% and the optical purity of the remaining chiral nonracemic ester compound was greater than 99% (48% chemical yield) after a 22 h reaction. These results are based on HPLC analysis of the remaining chiral nonracemic ester compound. The aqueous layer included hydrolyzed products (+)-FTC and (−)-FTC. The ratio of (+)-FTC and (−)-FTC was 96.6 to 3.4. The organic layer was evaporated to give 0.457 g of (−)-FTC butyrate.

Workup

  1. customgreater than 99% (48% chemical yield) after a 22 h
  2. customreaction
  3. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-6bdf46c6adba4db291176130a07d6ad7
Source dataset
uspto-grants-2005_12
Patent number
US06979561B1

Reaction notes

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