Triethylamine → HCID 13394189, compound

HRID 2164227Notes

Reaction equation

HRID 2164227 reaction equation
[C:1]([O:18][C@@H:19]1[C@@H:23]([CH2:24][O:25][C:26](=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[O:22][C@@H:21]([N:43]2[CH:50]=[C:49]([F:51])[C:47](=[O:48])[NH:46][C:44]2=[O:45])[CH2:20]1)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(N(CC)CC)C.[CH3:59][O:60][C:61]1[C:69]([O:70][CH3:71])=[CH:68][CH:67]=[CH:66][C:62]=1[C:63](Cl)=[O:64]>O1CCOCC1>[CH3:59][O:60][C:61]1[C:69]([O:70][CH3:71])=[CH:68][CH:67]=[CH:66][C:62]=1[C:63]([N:46]1[C:47](=[O:48])[C:49]([F:51])=[CH:50][N:43]([C@@H:21]2[O:22][C@H:23]([CH2:24][O:25][C:26](=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C@@H:19]([O:18][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:20]2)[C:44]1=[O:45])=[O:64]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27583922,3-Dimethoxybenzoyl chlorideHCID 99874467207-68-3

Product 1

HCID 13394189HCID 13394189, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.0 Grams of 2'-deoxy-3',5'-di-O-palmitoyl-5-fluorouridine are dissolved in 25 ml of dry dioxane and the solution is ice cooled. 2 Milliliters of triethylamine and 1.9 g of 2,3-dimethoxybenzoyl chloride are added to the solution and the mixture is subjected to reaction at room temperature for 10 minutes and then at 70° C. for 90 minutes. The reaction liquid is cooled and the precipitated triethylamine hydrochloride is filtered off. The filtrate is concentrated under reduced pressure and the residue is dissolved under heating in ethanol and the solution is allowed to stand whereby crystals are obtained which, after recrystallization from ethanol, affords 2.95 g (yield: 80.2%) of 3-(2,3-dimethoxybenzoyl)-2'-deoxy-3',5'-di-O-palmitoyl-5-fluorouridine. M.P. 77°-78° C.

Workup

  1. temperaturecooled
  2. customthe mixture is subjected to reaction at room temperature for 10 minutes
  3. customThe reaction liquid
  4. temperatureis cooled
  5. filtrationthe precipitated triethylamine hydrochloride is filtered off
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. dissolutionthe residue is dissolved
  8. temperatureunder heating in ethanol
  9. customare obtained which
  10. customafter recrystallization from ethanol

Sources & evidence

ORD record
ord-22dc25d3e98c4d4cbce4168ce2be1bd0
Source dataset
uspto-grants-1985_03
Patent number
US04503045

Reaction notes

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