Tetrahydrofuran → HCID 86641347, compound

HRID 1693314Notes

Reaction equation

HRID 1693314 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[C:15]2[CH2:14][S:13][N:12]=[C:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]3=[N:24][N:25]([CH2:27][C:28]4[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=4)[N:26]=[C:8]([C:9]=23)[CH:7]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.[OH-].[Na+]>O>[NH2:1][CH2:4][CH2:5][C:6]1[C:15]2[CH2:14][S:13][N:12]=[C:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[C:10]3=[N:24][N:25]([CH2:27][C:28]4[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=4)[N:26]=[C:8]([C:9]=23)[CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 86641348HCID 86641348, compound

Product 1

HCID 86641347HCID 86641347, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture composed of the above tert-butyl {8-(2-azidoethyl)-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}carbamate (31 mg), triphenylphosphine (23 mg), tetrahydrofuran (0.9 ml) and water (0.1 ml) was stirred at room temperature for five hours. A 0.2 N sodium hydroxide solution (2.5 ml) was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and filtered, and then the solvent in the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (NH silica used, ethyl acetate-chloroform) to obtain the title compound (17 mg) as an oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent in the filtrate was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (NH silica used, ethyl acetate-chloroform)

Sources & evidence

ORD record
ord-0300480d47814ea3bec39647e4ec81bb
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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