Stearoyl chloride → HCID 15009343, compound

HRID 1494502Notes

Reaction equation

HRID 1494502 reaction equation
[CH2:1]=[C:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]1=[O:12].[C:18](Cl)(=[O:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>N1C=CC=CC=1>[C:18]([NH:15][C:14]1[CH:16]=[CH:17][N:10]([C@@H:3]2[O:4][C@H:5]([CH2:8][O:9][C:18](=[O:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C@@H:6]([OH:7])[C:2]2=[CH2:1])[C:11](=[O:12])[N:13]=1)(=[O:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

4

Reactant 2

HCID 8212Stearoyl chlorideHCID 3005913119804-96-5

Product 1

HCID 15009343HCID 15009343, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2'-Deoxy-2'-methylidenecytidine, 239 mg, was dissolved in 5 ml of pyridine, 1.7 ml of stearoyl chloride was added portionwise under ice cooling, and the solution was stirred for 15 minutes. After the reaction, the reaction solution was partitioned with chloroform and the chloroform layer was distilled off under reduced pressure. The resulting residue was treated with silica gel chromatography (elution solvent: a mixture solvent of chloroform and methanol) to give the objective compound. m.p. 135°-139° C.

Workup

  1. customAfter the reaction
  2. customthe reaction solution was partitioned with chloroform
  3. distillationthe chloroform layer was distilled off under reduced pressure
  4. additionThe resulting residue was treated with silica gel chromatography (
  5. washelution solvent
  6. customa mixture solvent of chloroform and methanol) to give the objective compound

Sources & evidence

ORD record
ord-583897817693462382ea9151a6124833
Source dataset
uspto-grants-1991_06
Patent number
US05026835

Reaction notes

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