Formic Acid → HCID 58761948, compound

HRID 82289Notes

Reaction equation

HRID 82289 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[CH2:11]([O:13][C:14](=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1)[CH3:12].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH2:11]([O:13][C:14](=[O:23])[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][CH:1]=[O:3])=[CH:20][CH:21]=1)[CH3:12]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 58761948HCID 58761948, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of acetic anhydride (0.33 mL, 3.57 mmol) and formic acid (0.17 mL, 4.46 mmol) was heated at 60° C. for 2 hours. The reaction mixture was cooled to 0° C., a solution of (4-amino-phenyl)-acetic acid ethyl ester (Preparation 267, 500 mg, 2.79 mmol) in THF (10 mL) was added slowly to the reaction mixture and the reaction was allowed to stir at room temperature for 16 hours. The reaction mixture was neutralized with sat. aq. Na2CO3 solution and extracted with diethyl ether (2×25 mL). The combined organic layers were dried (Na2SO4) and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of DCM:MeOH 100:0 to 98:2) to afford the title compound as an oil in 93% yield, 500 mg.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionextracted with diethyl ether (2×25 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe crude material was purified by column chromatography on silica gel (gradient of DCM:MeOH 100:0 to 98:2)

Sources & evidence

ORD record
ord-9a4e48a8464d4692b330c33fb437e295
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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