Octanoyl chloride → HCID 136196924, compound

HRID 1638723Notes

Reaction equation

HRID 1638723 reaction equation
O.[OH:2][C@@H:3]([CH2:18][OH:19])[CH2:4][O:5][CH2:6][N:7]1[CH:15]=[N:14][C:13]2[C:12](=[O:16])[NH:11][C:10]([NH2:17])=[N:9][C:8]1=2.[C:20](Cl)(=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CN(C)C=O.N1C=CC=CC=1>[OH:2][C@H:3]([CH2:18][O:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][O:5][CH2:6][N:7]1[CH:15]=[N:14][C:13]2[C:12](=[O:16])[NH:11][C:10]([NH2:17])=[N:9][C:8]1=2

Participants

5

Reactant 2

HCID 8124Octanoyl chlorideHCID 136364563HCID 136364563, compound

Product 1

HCID 136196924HCID 136196924, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 410 mg (1.5 mmole) of (S)-9-(2,3-dihydroxy-1-propoxymethyl)guanine monohydrate in 6 ml of dry dimethylformamide and 1.5 ml of dry pyridine is stirred under a drying tube with cooling in an ice bath as a solution of 489 mg (3.0 mmole) of octanoyl chloride in 1.5 ml of dimethylformamide is added dropwise by syringe over approximately 5 minutes. The mixture is allowed to warm gradually to room temperature, and after 24 hours it is concentrated under high vacuum. The residual oil is purified by preparative TLC on nine 1000-μ silica gel plates (developed in 5:1 CHCl3 -MeOH). The product bands are isolated, combined, and extracted with dimethylformamide.

Workup

  1. additionis added dropwise by syringe over approximately 5 minutes
  2. concentrationafter 24 hours it is concentrated under high vacuum
  3. customThe residual oil is purified by preparative TLC on nine 1000-μ silica gel plates (developed in 5:1 CHCl3 -MeOH)
  4. customThe product bands are isolated
  5. extractionextracted with dimethylformamide

Sources & evidence

ORD record
ord-66e52aac05af428b9ceae69c83d0b97d
Source dataset
uspto-grants-1989_11
Patent number
US04880820

Reaction notes

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