Hydrochloric Acid → HCID 66999955, compound

HRID 560185Notes

Reaction equation

HRID 560185 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][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[CH:12][C:11]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:10][CH:9]=2)=[O:5])C.[OH-].[K+].CCOC(C)=O.Cl>C1COCC1.C(O)C.O>[C:28]1([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[C:14]3[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 66999450HCID 66999450, compound

Product 1

HCID 66999955HCID 66999955, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

5-Phenyl-3-[3-benzyloxycarbonyl-propyl]-1H-indole-2-carboxylic acid ethyl ester (40 mg, 0.088 mmol, 1.0 equiv) was dissolved in 4 mL of a 1:1 mixture of THF and ethanol. To this homogenous solution, KOH in water was added and the reaction mixture was stirred at 50° C. for 6 h. At this point TLC (100% EtOAc) showed only baseline material. The reaction was poured into 20 mL of 1 M HCl and was extracted 2×25 mL of EtOAc. The pooled organic fractions were dried (Na2SO4), filtered, and evaporated to yield 5-phenyl-3-[3-benzyloxycarbonyl-propyl]-1H-indole-2-carboxylic acid (34 mg, 90%).

Workup

  1. extractionwas extracted 2×25 mL of EtOAc
  2. dry with materialThe pooled organic fractions were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-51913bfe186b4138b8442c3804811b37
Source dataset
uspto-grants-2011_11
Patent number
US08063094B2

Reaction notes

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