Hydrochloric Acid → N-[(5-chloro-1H-indol-2-yl)carbonyl]glycine

HRID 651086Notes

Reaction equation

HRID 651086 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:20])[CH2:6][NH:7][C:8]([C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([Cl:19])=[CH:14][CH:13]=2)=[O:9].Cl>C1COCC1>[Cl:19][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:8]([NH:7][CH2:6][C:5]([OH:20])=[O:4])=[O:9])=[CH:18]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4893740methyl N-[(5-chloro-1H-indol-2-yl)carbonyl]glycinate

Product 1

HCID 11436686N-[(5-chloro-1H-indol-2-yl)carbonyl]glycine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

1N NaOH (35 ml) was added to a suspension of [(5-chloro-1H-indole-2-carbonyl)-amino]-acetic acid methyl ester (8.0 g, 30 mmol) in THF (100 ml) and the resulting mixture stirred for 18 hours at 25° C. The solution was acidified with 6N HCl (7 mL), the mixture concentrated, the solids suspended in water, filtered, and washed with water (7.42 g, 98%): HPLC (60/40) 2.89 minutes (100 %;)

Workup

  1. concentrationthe mixture concentrated
  2. filtrationfiltered
  3. washwashed with water (7.42 g, 98%)
  4. custom(60/40) 2.89 minutes (100 %;)

Sources & evidence

ORD record
ord-b5ef8e46b7134a1c84b676a640acc5c4
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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