Floxuridine → HCID 22851266, compound

HRID 1463972Notes

Reaction equation

HRID 1463972 reaction equation
[F:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.[C:18]([NH:21][C@@H:22]([C:26](O)=[O:27])[CH:23]([CH3:25])[CH3:24])(=[O:20])[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[C:18]([NH:21][C@@H:22]([C:26]([O:13][CH2:12][C@H:11]1[O:14][C@@H:7]([N:6]2[CH:15]=[C:2]([F:1])[C:3](=[O:17])[NH:4][C:5]2=[O:16])[CH2:8][C@@H:9]1[OH:10])=[O:27])[CH:23]([CH3:25])[CH3:24])(=[O:20])[CH3:19]

Participants

5

Reactant 4

HCID 5790FloxuridineHCID 11776TriphenylphosphineHCID 76475N-Acetyl-D-valineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 22851266HCID 22851266, compound

Procedure

To a solution of the active drug, preferably 2'-deoxy-5-fluorouridine, an N-protected amino acid, preferably N-acetyl-D-valine, and triphenylphosphine in an anhydrous polar aprotic solvent is added diisopropylazodicarboxylate. Upon completion of the reaction, the mixture is concentrated under reduced pressure. The prodrug, preferably a compound of Formula 11, most preferably, 2'-deoxy-5'-O-(N-acetyl-D-valinyl)-5-fluorouridine, may be isolated by conventional means.

Workup

  1. customUpon completion of the reaction
  2. concentrationthe mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-32072d5da1bd4e4bb6075f1dcb7755a1
Source dataset
uspto-grants-1994_04
Patent number
US05302707

Reaction notes

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