Ethyl orthoformate → HCID 68598108, compound

HRID 2090210Notes

Reaction equation

HRID 2090210 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:5]=[CH:6][NH:7][C:8](=[O:31])[C:9]=2[CH:10]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=2[O:27][C:26]([CH3:29])=[CH:25][C:24]3=[O:30])[C:11]=1[C:12]([O:14][CH2:15][CH2:16][C:17]#[N:18])=[O:13].C(OCC)(OCC)O[CH2:34][CH3:35]>S(=O)(=O)(O)O>[CH2:34]([O:31][C:8]1[N:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]([C:19]1[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=1[O:27][C:26]([CH3:29])=[CH:25][C:24]3=[O:30])[C:11]([C:12]([O:14][CH2:15][CH2:16][C:17]#[N:18])=[O:13])=[C:2]([CH3:1])[NH:3]2)[CH3:35]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 68601724HCID 68601724, compound

Product 1

HCID 68598108HCID 68598108, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
130 °C

Procedure

2.20 g (5.27 mmol) of the compound from Example 31A are suspended in 80 ml of triethyl orthoformate and heated to 130° C. Then, over a total period of 8 hours, 5 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: initially dichloromethane, then ethyl acetate, finally ethyl acetate/methanol 20:1). The product fractions are concentrated to a volume of about 5 ml. The precipitated product is filtered off and, after washing with ethyl acetate and diethyl ether, dried under high vacuum. 282 mg (12% of theory) of the title compound are obtained in the form of brown crystals.

Workup

  1. temperatureAfter cooling
  2. customexcess orthoester is removed in a rotary evaporator
  3. customthe crude product is purified by column chromatography (silica gel
  4. concentrationThe product fractions are concentrated to a volume of about 5 ml
  5. filtrationThe precipitated product is filtered off
  6. washafter washing with ethyl acetate and diethyl ether
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-4c89b358def9412ebd89967a15308d8b
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

Loading…