Methyl L-phenylalaninate hydrochloride → HCID 10546217, compound

HRID 651083Notes

Reaction equation

HRID 651083 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25](O)=[O:26])=[CH:19]2>>[CH3:2][O:3][C:4](=[O:14])[C@@H:5]([NH:6][C:25]([C:20]1[NH:21][C:22]2[C:18]([CH:19]=1)=[CH:17][C:16]([Cl:15])=[CH:24][CH:23]=2)=[O:26])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 826935-Chloro-1H-indole-2-carboxylic acid

Product 1

HCID 10546217HCID 10546217, compound

Procedure

L-Phenylalanine methyl ester hydrochloride (77.0 mmol) and 5-chloro-1 H-indole-2-carboxylic acid (77 mmol) were coupled according to procedure A (0-25° C.) and the product purified by chromatography on silica gel in 10 and 20% ethyl acetate-hexanes giving the title substance as an off-white solid (22.12 g, 81%): mp 156-157° C.; HPLC (60/40) 9.5 minutes (98%); PBMS 357/359 (MH+, 100%).

Workup

  1. customwere coupled according to procedure A (0-25° C.)
  2. customthe product purified by chromatography on silica gel in 10 and 20% ethyl acetate-hexanes giving the title substance as an off-white solid (22.12 g, 81%)
  3. customHPLC (60/40) 9.5 minutes (98%)

Sources & evidence

ORD record
ord-69dba2ab55ab4b6eb9c3e6f75e917bb1
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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