Citric Acid → HCID 24769674, compound

HRID 1889274Notes

Reaction equation

HRID 1889274 reaction equation
C[O:2][C:3](=[O:24])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:21][CH2:22][OH:23])=[O:9])([CH3:6])[CH3:5].[CH2:25]1[C:33]2[C:28](=[CH:29][C:30](O)=[CH:31][CH:32]=2)[CH2:27][CH2:26]1.CCOC(/N=N/C(OCC)=O)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.C(OCC)(=O)C>[CH2:25]1[C:33]2[C:28](=[CH:29][C:30]([O:23][CH2:22][CH2:21][O:20][C:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:18]=[CH:19][C:10]=3[C:8]([NH:7][C:4]([CH3:5])([CH3:6])[C:3]([OH:2])=[O:24])=[O:9])=[CH:31][CH:32]=2)[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 151185-IndanolHCID 5462977Diethyl azodicarboxylateHCID 68842699HCID 68842699, compound

Product 1

HCID 24769674HCID 24769674, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under inert atmosphere to 166 mg 2-{[1-(2-hydroxy-ethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester, 74 mg indan-5-ol and 208 mg polystyrene-bound triphenyl phosphine (3 mmol/g) in 5 ml THF at 0° C. 98 μl diethylazodicarboxylate were added. After 16 h at room temperature the reaction was filtrated, the filtrate concentrated in vacuo and after RP-HPLC the obtained 2-({1-[2-(Indan-5-yloxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid methyl ester was dissolved in 3 ml of dioxane and reacted with 3 ml 1N NaOH for 5 h at 50° C. The reaction was then diluted with ethyl acetate and treated with citric acid (5%). The organic layer was separated, dried and concentrated in vacuo. After purification by RP-HPLC 22 mg 2-{[1-(2-hydroxy-ethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid were obtained.

Workup

  1. customat 0° C
  2. filtrationAfter 16 h at room temperature the reaction was filtrated
  3. concentrationthe filtrate concentrated in vacuo
  4. dissolutionafter RP-HPLC the obtained 2-({1-[2-(Indan-5-yloxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid methyl ester was dissolved in 3 ml of dioxane
  5. customreacted with 3 ml 1N NaOH for 5 h at 50° C
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customAfter purification by RP-HPLC 22 mg 2-{[1-(2-hydroxy-ethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid
  10. customwere obtained

Sources & evidence

ORD record
ord-a1cf88baf26045c0a5534a8a3a5e8981
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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