5-Chloro-1H-indole-2-carboxylic acid → (+/-)-[(5-Chloro-1h-indole-2-carbonyl)-amino]-3-hydroxy-propionic acid methyl ester

HRID 651107Notes

Reaction equation

HRID 651107 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[CH:5]([CH2:7][OH:8])[NH2:6].[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20](O)=[O:21])=[CH:14]2>>[CH3:2][O:3][C:4](=[O:9])[CH:5]([NH:6][C:20]([C:15]1[NH:16][C:17]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:10])=[CH:19][CH:18]=2)=[O:21])[CH2:7][OH:8]

Participants

3

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 517373Methyl DL-serinate hydrochloride

Product 1

HCID 53751358(+/-)-[(5-Chloro-1h-indole-2-carbonyl)-amino]-3-hydroxy-propionic acid methyl ester

Procedure

D,L-Serine methyl ester hydrochloride (2.1 mmol) and 5-chloro-1H-indole-2-carboxylic acid (2.0 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, washed with acid first then with saturated NaHCO3) and the product purified by chromatography on silica gel eluted with 10, 20, 40 and 60% ethyl acetate in hexanes: Yield 565 mg, 95%; HPLC (60/40) 3.46 minutes (98%); mp 153-155 ° C.; TSPMS 297/299 (MH+, 100/40%);

Workup

  1. custom0-25° C. reaction temperature
  2. washwashed with acid first
  3. customwith saturated NaHCO3) and the product purified by chromatography on silica gel
  4. washeluted with 10, 20, 40 and 60% ethyl acetate in hexanes
  5. customHPLC (60/40) 3.46 minutes (98%)

Sources & evidence

ORD record
ord-03b7931c3f1f40fb9a553f75768dce56
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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