Citric Acid → HCID 52934125, compound

HRID 1887022Notes

Reaction equation

HRID 1887022 reaction equation
O=[C:2]1[N:21]([CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2=[N:6][C:7]([C:10]3[CH:11]=[N:12][N:13]4[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][C:14]=34)=[CH:8][CH:9]=[C:4]2[NH:3]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(OCC)OCC>CCO>[O:25]1[CH2:24][CH2:23][CH:22]([N:21]2[C:5]3=[N:6][C:7]([C:10]4[CH:11]=[N:12][N:13]5[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][C:14]=45)=[CH:8][CH:9]=[C:4]3[N:3]=[CH:2]2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 31214Ethyl orthoformateHCID 67123825HCID 67123825, compound

Product 1

HCID 52934125HCID 52934125, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
145 °C

Procedure

To a suspension of the compound obtained in example 2 section d (33.6 mg, 0.1 mmol) in EtOH (1.5 mL), citric acid (2 mg, 0.1 mmol) and triethyl orthoformate (340 μL, 2 mmol) were added. The reaction mixture was heated in a CEM Explorer microwave oven at 145° C. and 270 W for 2.5 hours. The crude residue was chromatographed on a silica gel flash system (ISCO Rf) using hexanes/acetone mixtures of increasing polarity as eluent to afford 14.2 mg of the desired product (41% yield).

Workup

  1. customThe crude residue was chromatographed on a silica gel flash system (ISCO Rf)
  2. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-a112c58e8cde48b8b84a3675e40a9952
Source dataset
uspto-grants-2013_08
Patent number
US08501735B2

Reaction notes

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