Chloroform → HCID 15858377, compound

HRID 442702Notes

Reaction equation

HRID 442702 reaction equation
[O:1]1[CH:3]([CH2:4][S:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:2]1.[NH:24]1[CH:31]=[CH:30][C:28]([NH2:29])=[N:27][C:25]1=[O:26].C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl>CN(C)C=O>[OH:1][CH:3]([CH2:4][S:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:2][N:24]1[CH:31]=[CH:30][C:28]([NH2:29])=[N:27][C:25]1=[O:26]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 13417926HCID 13417926, compoundHCID 178418229Cytosine

Product 1

HCID 15858377HCID 15858377, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

rac-1,2-Epoxy-3-octadecylthiopropane (2.0 g, 5.83 mmol) is added to a mixture of cytosine (1.0 g, 9.0 mmol) and anhydrous potassium carbonate (40 mg) in dimethyl formamide (25 mL) over a 30 minute period under a nitrogen atmosphere. The resultant mixture is stirred at 80°-90° C. (oil bath temperature) for 48 hours. The reaction mixture is cooled to room temperature and concentrated in vacuo to leave a residue. The residue is stirred with chloroform (50 mL). The undissolved material is filtered in vacuo, and the filtrate concentrated in vacuo, purified by chromatography and dried in vacuo to afford 1-[2'-hydroxy-3'-octadecylthiopropyl]-cytosine.

Workup

  1. concentrationconcentrated in vacuo
  2. customto leave a residue
  3. filtrationThe undissolved material is filtered in vacuo
  4. concentrationthe filtrate concentrated in vacuo
  5. custompurified by chromatography
  6. customdried in vacuo

Sources & evidence

ORD record
ord-113c475e838d44d084d9239d610ccf5f
Source dataset
uspto-grants-1999_04
Patent number
US05891881

Reaction notes

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