Palmitoyl chloride → 3',5'-Di-palmitoyl-2'-deoxy-2'-(N-Fmoc-beta-alanineamido)uridine

HRID 1987789Notes

Reaction equation

HRID 1987789 reaction equation
[C:1](Cl)(=[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:19]([N:36]([C@@H:42]1[C@H:46]([OH:47])[C@@H:45]([CH2:48][OH:49])[O:44][C@H:43]1[N:50]1[CH:57]=[CH:56][C:54](=[O:55])[NH:53][C:51]1=[O:52])[C:37](=[O:41])[CH2:38][CH2:39][NH2:40])([O:21][CH2:22][CH:23]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20]>N1C=CC=CC=1>[C:1]([C@@:46]1([OH:47])[C@@H:45]([CH:48]([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])[OH:49])[O:44][C@@H:43]([N:50]2[CH:57]=[CH:56][C:54](=[O:55])[NH:53][C:51]2=[O:52])[C@@H:42]1[N:36]([C:19]([O:21][CH2:22][CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]2[C:35]1=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:20])[C:37](=[O:41])[CH2:38][CH2:39][NH2:40])(=[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]

Participants

4

Reactant 2

HCID 8206Palmitoyl chlorideHCID 686614692'-Deoxy-2'-(N-Fmoc-beta-alanineamido)uridine

Product 1

HCID 865876713',5'-Di-palmitoyl-2'-deoxy-2'-(N-Fmoc-beta-alanineamido)uridineYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Palmitoyl chloride (1.55 mL, 1.8 mmol) was added to a solution of nucleoside 28 in abs pyridine and the reaction mixture was stirred overnight at room temperature. The solution was then quenched with MeOH, evaporated to dryness, dissolved in dichloromethane and washed with saturated aq sodium bicarbonate and brine. The organic phase was dried oversodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica (EtOAc-Hexanes 1:1) affording 0.5 g of 29 (yield, 65%).

Workup

  1. customThe solution was then quenched with MeOH
  2. customevaporated to dryness
  3. dissolutiondissolved in dichloromethane
  4. washwashed with saturated aq sodium bicarbonate and brine
  5. dry with materialThe organic phase was dried oversodium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography on silica (EtOAc-Hexanes 1:1)

Sources & evidence

ORD record
ord-f4ef13facbc54a178f202332425b6361
Source dataset
uspto-grants-2009_06
Patent number
US07553830B2

Reaction notes

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