Sulfuric Acid → HCID 23196286, compound

HRID 726536Notes

Reaction equation

HRID 726536 reaction equation
[CH2:1]([CH2:5][CH:6]=O)[CH2:2][CH:3]=O.S(=O)(=O)(O)O.[CH2:13]([O:15][P:16]([CH2:21][N:22]1[C:31]2[CH:30]=[C:29]([NH2:32])[C:28]3[CH:33]=[CH:34][CH:35]=[CH:36][C:27]=3[C:26]=2[NH:25][C:24](=[O:37])[C:23]1=[O:38])(=[O:20])[O:17][CH2:18][CH3:19])[CH3:14].[BH4-].[Na+].B([O-])[O-].[Na+].[Na+]>O1CCCC1.O1CCCC1.CO>[CH2:13]([O:15][P:16]([CH2:21][N:22]1[C:31]2[CH:30]=[C:29]([N:32]3[CH2:6][CH2:5][CH2:1][CH2:2][CH2:3]3)[C:28]3[CH:33]=[CH:34][CH:35]=[CH:36][C:27]=3[C:26]=2[NH:25][C:24](=[O:37])[C:23]1=[O:38])(=[O:20])[O:17][CH2:18][CH3:19])[CH3:14]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 3485GlutaraldehydeHCID 4311764Sodium borohydrideHCID 23196302HCID 23196302, compoundHCID 178507093HCID 178507093, compound

Product 1

HCID 23196286HCID 23196286, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 100 microliters of aqueous glutaric dialdehyde (content about 25%), 300 microliters of diluted sulfuric acid and 1 ml of tetrahydrofuran/methanol 1:1 is added with stirring at ice bath temperature to 37 mg of (6-amino-2,3-dioxo-1,2,3,4-tetrahydrobenzo[f]quinoxalin-4-yl)-methanephosphonic acid diethyl ester in 2 ml of tetrahydrofuran z.A., to which 13 mg of sodium borohydride was added. Then, another 10 mg of sodium boronate is added and worked up for 1 more hour. The mixture is neutralized and extracted with ethyl acetate. After chromatography with a little silica gel, 16 mg of product is obtained.

Workup

  1. additionis added
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-cf6179b3a9c04635a0f828bb1b30f5fb
Source dataset
uspto-grants-1998_01
Patent number
US05710138

Reaction notes

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