Chloroform → 1-[2'-Hydroxy-3'-octadecyloxypropyl]-cytosine

HRID 442699

Reaction equation

HRID 442699 reaction equation
[O:1]1[CH:3]([CH2:4][O: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][O: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 61831Oxirane, 2-[(octadecyloxy)methyl]-HCID 178418229Cytosine

Product 1

HCID 158583761-[2'-Hydroxy-3'-octadecyloxypropyl]-cytosineYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

rac-1,2-Epoxy-3-octadecyloxypropane (2.0 g, 6.13 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 is concentrated in vacuo, purified by chromatography and dried in vacuo to afford 1.0 g (37%) of 1-[2'-hydroxy-3'-octadecyloxypropyl]-cytosine (CPR 1149): Thin-layer Chromatography (TLC; 4×8 cm silica gel 60, 0.25 mm thickness): 10:2:0.2 (v/v/v) CHCl3 -CH3OH-30% aqueous ammonia (Rf value=0.66); mp 153°-154° C.

Workup

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

Sources & evidence

ORD record
ord-74fdd7d75b3f43d88bc3d2c8530536f5
Source dataset
uspto-grants-1999_04
Patent number
US05891881

Linked notes

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