Hydrochloric Acid → HCID 10717419, compound

HRID 2292817Notes

Reaction equation

HRID 2292817 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]([CH3:28])=[C:15]3[CH2:29][C:30]([NH2:32])=[O:31])[CH:5]=1.[OH-].[Na+].Cl>C1COCC1.C(O)C>[NH2:32][C:30](=[O:31])[CH2:29][C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([O:11][CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:33])=[O:2])[CH:13]=2)[N:17]([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]=1[CH3:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11797459HCID 11797459, compound

Product 1

HCID 10717419HCID 10717419, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 470 mg (1.06 mmol) of 3-[[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]methyl]benzoic acid methyl ester and 2 mL of 2N NaOH in 10 mL of THF and 40 mL of ethanol was stirred for 7.5 hours, the mixture made acidic with 5N HCl and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (Na2SO4) and concentrated at reduced pressure. The residue was crystallized from methylene chloride/ethanol to give 330 mg (72% yield) of 3-[[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]methyl]benzoic acid, mp, 176°-179° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate solution was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was crystallized from methylene chloride/ethanol

Sources & evidence

ORD record
ord-39937fb273464b62a8dd50a0234fc3e0
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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