tert-Butanol → HCID 57855964, compound

HRID 2039600Notes

Reaction equation

HRID 2039600 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1C(O)=O)[N:11]=[CH:10][CH:9]=[N:8]2)=[O:4].CC[N:20]([CH2:23]C)CC.C1C=CC([O:31]P(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45]>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[NH:20][C:23]([O:48][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:31])[N:11]=[CH:10][CH:9]=[N:8]2)=[O:4]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 57855888HCID 57855888, compound

Product 1

HCID 57855964HCID 57855964, compoundYield 80%

Conditions

Temperature
85 °C

Procedure

7.1 g (30.6 mmol) quinoxaline-6,7-dicarboxylic acid monomethyl ester, 8 ml NEt3, 1 g molecular sieve 4 Å and 10 ml (46.40 mmol) diphenylphosphonic azide is successively added to 100 ml t-butanol. The mixture is heated at a temperature of 85° C. during 20 hours. After cooling, the mixture is filtered and the solid is washed with 1000 ml THF. The filtrate is evaporated and submitted to flash-chromatography to give 7.45 g (80%) of the title compound. m.p.: 196-198° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. washthe solid is washed with 1000 ml THF
  4. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-556544fd5bb64fd0b0eadf7fda569fa1
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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