Hydrochloric Acid → HCID 58172097, compound

HRID 560172Notes

Reaction equation

HRID 560172 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:12][C:11]([Br:26])=[CH:10][CH:9]=2)=[O:5])C.O.[OH-].[Li+].Cl>CO.C1COCC1.O>[Br:26][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[C:14]2[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58172020HCID 58172020, compound

Product 1

HCID 58172097HCID 58172097, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

5-Bromo-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester (65 mg, 0.15 mmol, 1.0 equiv) was dissolved in 10 mL of 1:1 methanol/THF. To this was added a solution of lithium hydroxide hydrate (200 mg, 4.8 mmol, 31 equiv) in 5 mL water. The reaction was heated at 50° C. for 15 min and then stirred at ambient temperature overnight. The reaction was cooled to 0° C. and acidified to pH˜2 with concentrated HCl. The product was extracted with ethyl acetate (2×25 mL). The solution was dried over anhydrous sodium sulfate, filtered, and evaporated to give 55 mg of 5-bromo-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid (55 mg, 91%). This material was used without further manipulation.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. extractionThe product was extracted with ethyl acetate (2×25 mL)
  3. dry with materialThe solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-59c0b56352e841599c2fbf8c097fe65d
Source dataset
uspto-grants-2011_11
Patent number
US08063094B2

Reaction notes

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