Hydrochloric Acid → HCID 9951750, compound

HRID 2303527Notes

Reaction equation

HRID 2303527 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C:24](=[O:28])[C:25]([NH2:27])=[O:26])=[C:9]([CH2:22][CH3:23])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].CO.Cl>CCOC(C)=O>[NH2:27][C:25](=[O:26])[C:24]([C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[NH:5][CH2:4][C:3]([OH:29])=[O:2])[N:10]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:9]=1[CH2:22][CH3:23])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 10691962[[3-(Aminooxoacetyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]amino]acetic acid methyl ester

Product 1

HCID 9951750HCID 9951750, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 190 mg (0.48 mmol) of [[3-(Aminooxoacetyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]amino]acetic acid methyl ester, 5 ml of 1N NaOH, and 15 ml of MeOH was refluxed 0.33 hour, cooled, and stirred at room temperature for 1 hour. EtOAc and acqueous HCl were added and the EtOAc layer was washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was crystallized from MeOH to give 96 mg (53%) of ([3-(Aminooxoacetyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]amino]ac(e,tic acid melting at 151-157° C.

Workup

  1. temperaturewas refluxed 0.33 hour
  2. temperaturecooled
  3. washthe EtOAc layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was crystallized from MeOH
  7. customto give 96 mg (53%) of ([3-(Aminooxoacetyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]amino]ac(e,tic acid melting at 151-157° C.

Sources & evidence

ORD record
ord-cc4008ca31654f728ea53e176d2a85fc
Source dataset
uspto-grants-2002_08
Patent number
US06433001B1

Reaction notes

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