Hydrochloric Acid → HCID 54689826, compound

HRID 1244090Notes

Reaction equation

HRID 1244090 reaction equation
[H-].[Na+].C(OC([C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:11][S:10][C:9]=1[NH:20][C:21](=[O:28])[CH2:22][C:23]([O:25]CC)=O)=O)C.Cl>C1COCC1.CO.[OH-].[Na+]>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]2[C:8]3[C:23]([OH:25])=[CH:22][C:21](=[O:28])[NH:20][C:9]=3[S:10][CH:11]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69607336HCID 69607336, compound

Product 1

HCID 54689826HCID 54689826, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60% suspension in mineral oil, pre washed with hexanes, 0.430 g, 10.73 mmol) in THF (25 mL) was added a solution of 4-(4-chlorophenyl)-2-(2-ethoxycarbonyl acetylamino)-thiophene-3-carboxylic acid ethyl ester (1.9308 g, 4.88 mmol) in THF (25 mL) dropwise via syringe. The reaction mixture was then heated to reflux for 3 hrs, cooled to 0° C. and quenched by dropwise addition of MeOH (5 mL) and H2O (2 mL). The reaction mixture was concentrated to give a crude solid which was then dissolved in MeOH (30 mL) and 40% NaOH (30 mL). The resulting mixture was heated at for 5 hours, cooled to room temperature and acidified with concentrated HCl. The mixture was concentrated under reduced pressure and DMSO/MeOH (1:1) was used to dissolve the residue and filtered. The filtrate was purified on a RP-HPLC system to afford the title compound. MS (ESI) m/e 275.9 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 11.55 (br s, 1H), 10.92 (s, 1H), 7.47–7.39 (m, 4H), 7.06 (s, 1H), 5.74 (s, 3H).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 3 hrs
  3. customquenched by dropwise addition of MeOH (5 mL) and H2O (2 mL)
  4. concentrationThe reaction mixture was concentrated
  5. customto give a crude solid which
  6. temperatureThe resulting mixture was heated at for 5 hours
  7. temperaturecooled to room temperature
  8. concentrationThe mixture was concentrated under reduced pressure and DMSO/MeOH (1:1)
  9. dissolutionto dissolve the residue
  10. filtrationfiltered
  11. customThe filtrate was purified on a RP-HPLC system

Sources & evidence

ORD record
ord-f09f643350434bee882becb7632a10cd
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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