Water → (6-Nitro-7-morpholino-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl)methanephosphonic acid

HRID 1289455Notes

Reaction equation

HRID 1289455 reaction equation
C([O:3][P:4]([CH2:9][N:10]1[C:19]2[C:14](=[CH:15][C:16]([N+:26]([O-:28])=[O:27])=[C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:18]=2)[NH:13][C:12](=[O:29])[C:11]1=[O:30])(=[O:8])[O:5]CC)C.C[Si](C)(C)Br.O>C(#N)C>[N+:26]([C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][C:17]=1[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[N:10]([CH2:9][P:4]([OH:5])(=[O:3])[OH:8])[C:11](=[O:30])[C:12](=[O:29])[NH:13]2)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 17800789(6-Nitro-7-morpholino-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl)methanephosphonic acid diethyl ester

Product 1

HCID 21847686(6-Nitro-7-morpholino-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl)methanephosphonic acidYield 26.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

259 mg of (6-nitro-7-morpholino-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl)methanephosphonic acid diethyl ester is mixed in 10 ml of absolute acetonitrile with 628 mg of trimethylbromosilane and stirred for 1 hour at room temperature. A little water is added, and it is evaporated to dryness. The residue is chromatographed on silanized silica gel with methanol as eluant. 60 mg of (6-nitro-7-morpholino-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl)methanephosphonic acid is obtained.

Workup

  1. customit is evaporated to dryness
  2. customThe residue is chromatographed on silanized silica gel with methanol as eluant

Sources & evidence

ORD record
ord-534167ffe68a42648f1fad12814fe8b8
Source dataset
uspto-grants-1998_05
Patent number
US05750525

Reaction notes

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