Diethyl Ether → HCID 136461466, compound

HRID 1194802Notes

Reaction equation

HRID 1194802 reaction equation
O.[OH:2][CH2:3][CH:4]([O:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:14](=[O:18])[NH:13][C:12]([NH2:19])=[N:11][C:10]1=2)[CH2:5][OH:6].[C:20](Cl)(=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].CCOCC>CN(C)C=O.N1C=CC=CC=1>[OH:2][CH2:3][CH:4]([O:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:14](=[O:18])[NH:13][C:12]([NH2:19])=[N:11][C:10]1=2)[CH2:5][O:6][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 8124Octanoyl chlorideHCID 1360789939-[[2-Hydroxy-1-(hydroxymethyl)ethoxy]methyl]guanine hydrate

Product 1

HCID 136461466HCID 136461466, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 410 mg (1.5 mmole) of 9-(1,3-dihydroxy-2-propoxymethyl)guanine monohydrate in 6 ml of dry dimethylformamide and 1.5 ml of dry pyridine was 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 was added dropwise by syringe over approximately 5 minutes. The mixture was allowed to warm gradually to room temperature, and after 24 hours it was concentrated under high vacuum. The residual oil was purified by preparative TLC on nine 1000-μ silica gel plates (developed in 5:1 CHCl3 --MeOH). The product bands were isolated, combined, and extracted with dimethylformamide. Concentration of the extracts under high vacuum gave a gummy residue. Crystallization from isopropanol gave a material which again turned gummy on the filter. However, thorough trituration with ether yielded 105 mg (18%) of very pale yellow crystals, m.p. 201.5°-203.5°.

Workup

  1. additionwas added dropwise by syringe over approximately 5 minutes
  2. concentrationafter 24 hours it was concentrated under high vacuum
  3. customThe residual oil was purified by preparative TLC on nine 1000-μ silica gel plates (developed in 5:1 CHCl3 --MeOH)
  4. customThe product bands were isolated
  5. extractionextracted with dimethylformamide
  6. customConcentration of the extracts under high vacuum gave a gummy residue
  7. customCrystallization from isopropanol
  8. customgave a material which again turned gummy on the filter

Sources & evidence

ORD record
ord-ed2de38ea7ad4beb8bd8fd553338973f
Source dataset
uspto-grants-1989_03
Patent number
US04816447

Reaction notes

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