Formic Acid → HCID 56602320, compound

HRID 514041Notes

Reaction equation

HRID 514041 reaction equation
C([O:3][C:4](=[O:31])[CH:5]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:17][CH3:18])[C:7]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)C.[Li+].[OH-].[OH-].[Na+].C(O)=O>C1COCC1.CCO>[C:27]([O:26][CH:5]([C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:17][CH3:18])[C:7]=1[C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[C:4]([OH:31])=[O:3])([CH3:30])([CH3:28])[CH3:29]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 67126266HCID 67126266, compound

Product 1

HCID 56602320HCID 56602320, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butoxy-[1-(4-chloro-phenyl)-5-methoxy-3-methyl-naphthalen-2-yl]-acetic acid ethyl ester (12 mg) in THF (0.3 mL) and EtOH (0.1 mL) was added 0.1 mL of 1 M LiOH. The reaction was stirred for 30 min at room temperature, then 0.3 mL each of THF, EtOH, and 1 M NaOH were added. The reaction was heated to 70° C. for 2.5 hours, and then cooled to room temperature. Formic acid was added until pH ˜5. The reaction mixture was directly purified by HPLC (Gemini, 50-100% MeCN/H2O, with 0.1% TFA). The product was lyophilized to give a white powder (8 mg).

Workup

  1. temperatureThe reaction was heated to 70° C. for 2.5 hours
  2. temperaturecooled to room temperature
  3. customThe reaction mixture was directly purified by HPLC (Gemini, 50-100% MeCN/H2O, with 0.1% TFA)

Sources & evidence

ORD record
ord-da826d65f8444866aa33979b8e6aa27d
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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