Hydrochloric Acid → HCID 10623063, compound

HRID 2292816Notes

Reaction equation

HRID 2292816 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]([CH2:28][CH3:29])=[C:15]2[CH2:30][C:31]([NH2:33])=[O:32].[OH-].[Na+].Cl>C(O)C>[NH2:33][C:31](=[O:32])[CH2:30][C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([O:11][CH2:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:34])=[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[CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10623682HCID 10623682, compound

Product 1

HCID 10623063HCID 10623063, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 495 mg (1.08 mmol) of 2-[[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]methyl]benzoic acid methyl ester and 2 mL of 5N NaOH in 25 mL of ethanol was stirred for 17 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/ether to give 440 mg (92% yield) of 2-[[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]methyl]benzoic acid, mp, approximately 100° 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/ether

Sources & evidence

ORD record
ord-812633c23c4a42f0b05b3fe04c8f8b12
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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