Water → HCID 15599535, compound

HRID 2210878Notes

Reaction equation

HRID 2210878 reaction equation
[OH:1][C@H:2]([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][CH3:19])[C:3]([OH:5])=[O:4].[C:20](OC(=O)C)(=[O:22])[CH3:21].C(OCC)(=O)C.O>N1C=CC=CC=1>[C:20]([O:1][C@H:2]([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][CH3:19])[C:3]([OH:5])=[O:4])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 11065598(R)-2OH PA

Product 1

HCID 15599535HCID 15599535, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To (R)-(+)-2-hydroxyhexadecanoic acid (0.5 g; prepared according to the method described in Agric. Biol. Chem., 54(12), 3337-3338, 1990) dissolved in pyridine (15 ml) was added acetic anhydride (0.23 ml) at 0° C., and the mixture was stirred 12 hours. The reaction mixture was distributed into ethyl acetate and water, and the ethyl acetate layer was dried and concentrated to give (R)-(-)-2-acetoxyhexadecanoic acid (0.52 g). The acetoxy derivative was dissolved in DMF (20 ml), and N-hydroxysuccinimide (191 mg) and N,N'-dicyclohexylcarbodiimide (342 mg) were added to the solution at 0° C. The mixture was stirred at room temperature for 12 hours. The reaction mixture was then filtered, and 6-(4'-N-glycyl-spicaminyl-amino)purine hydrochloride (0.65 g) and triethylamine (1.1 ml) were added to the filtrate. The mixture was stirred for 12 hours. After the reaction mixture was concentrated, the residue was subjected to chromatography on a silica gel column with eluent systems of chloroform-methanol (from 7:1 to 5:1) to give SPK198 in the yield of 119 mg.

Workup

  1. customprepared
  2. dry with materialthe ethyl acetate layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-41a103d049084b6cb659439fe255619f
Source dataset
uspto-grants-1995_10
Patent number
US05461036

Reaction notes

Loading…