Ethyl orthoformate → HCID 68600031, compound

HRID 2090200Notes

Reaction equation

HRID 2090200 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:17](=[O:19])[NH:16][CH:15]=[CH:14][C:13]=3[NH:12][C:11]([CH3:20])=[C:10]2[C:21]([O:23][CH2:24][CH2:25][C:26]#[N:27])=[O:22])=[C:5]([O:28][CH3:29])[CH:4]=1)#[N:2].C(OCC)(OCC)O[CH2:32][CH3:33]>S(=O)(=O)(O)O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[N:16][C:17]=3[O:19][CH2:32][CH3:33])[NH:12][C:11]([CH3:20])=[C:10]2[C:21]([O:23][CH2:24][CH2:25][C:26]#[N:27])=[O:22])=[C:5]([O:28][CH3:29])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 68599096HCID 68599096, compound

Product 1

HCID 68600031HCID 68600031, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
130 °C

Procedure

10.00 g (25.62 mmol) of the compound from Example 20A are suspended in 250 ml of triethyl orthoformate and heated to 130° C. Then, over a total period of 8 hours, 15 drops of concentrated sulfuric acid are added each hour to the reaction mixture. It is then stirred at the same temperature overnight. After cooling, excess orthoester is removed in a rotary evaporator, and the crude product is purified by column chromatography (silica gel; mobile phase: cyclohexane/ethyl acetate 1:1). 7.20 g (65% of theory) of the title compound are obtained.

Workup

  1. temperatureAfter cooling
  2. customexcess orthoester is removed in a rotary evaporator
  3. customthe crude product is purified by column chromatography (silica gel; mobile phase: cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-e3dab59d8d64436e97ed16bcdd9d47d6
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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