HCID 68283589, compound → HCID 68283907, compound

HRID 1527222Notes

Reaction equation

HRID 1527222 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]CC3C=CC=CC=3)=[CH:14][CH:15]=2)[C:10]([C:25](=[O:27])[NH2:26])=[CH:9]1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:25](=[O:27])[NH2:26])=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 68283589HCID 68283589, compound

Product 1

HCID 68283907HCID 68283907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5-Benzyloxy-3-carbamoyl-indol-1-yl)-acetic acid tert-butyl ester (250 mg, 0.657 mmol) was suspended in THF (13 mL). Air was removed from the flask and replaced with nitrogen three times. Pd/C 10% (25 mg) was added to the solution which was again degassed, placed under a hydrogen atmosphere and stirred at RT overnight. The catalyst was removed through a 0.45 microns filter and concentrated in vacuo. The crude material was purified by preparative HPLC (SunFire C18-ODB, 5 μm, 30×100 mm, eluent: 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 40 mL/min) to give after lyophilization of the purified fractions the desired compound as a white solid. MS: 291 [M+H]+, 313 [M+Na]+, 581 [2M+H]+, 603 [2M+Na]+; tR (HPLC conditions c): 3.75 min.

Workup

  1. customAir was removed from the flask
  2. additionPd/C 10% (25 mg) was added to the solution which
  3. customwas again degassed
  4. customThe catalyst was removed through a 0.45 microns
  5. filtrationfilter
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by preparative HPLC (SunFire C18-ODB, 5 μm, 30×100 mm, eluent: 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 40 mL/min)
  8. customto give after lyophilization of the
  9. custompurified fractions the desired compound as a white solid
  10. custom3.75 min.

Sources & evidence

ORD record
ord-3ee67649e4e2470c9f2ce2d5afd77607
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…