5-Chloro-1H-indole-2-carboxylic acid → HCID 57296325, compound

HRID 651126Notes

Reaction equation

HRID 651126 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]([N:6]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7]1)=[O:5].[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29](O)=[O:30])=[CH:23]2>>[CH2:12]([C@H:3]([NH:2][C:29]([C:24]1[NH:25][C:26]2[C:22]([CH:23]=1)=[CH:21][C:20]([Cl:19])=[CH:28][CH:27]=2)=[O:30])[C:4](=[O:5])[N:6]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 69688732HCID 69688732, compound

Product 1

HCID 57296325HCID 57296325, compound

Procedure

(S)-1-(2-Amino-3-phenyl-propionyl)-pyrrolidin-3-one hydrochloride (0.6 mmol) and 5-chloro-1H-indole-2-carboxylic acid (0.6 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, washed with acid first, then base) and the product purified by chromatography on silica gel eluted with 40 and 50% ethyl acetate in hexanes, followed by trituration of the resulting foam with ether. Yield 112 mg, 45%; HPLC (60/40) 5.13 minutes (>99%); PBMS 410/412 (MH+, 100%);

Workup

  1. custom0-25° C. reaction temperature
  2. washwashed with acid first
  3. custombase) and the product purified by chromatography on silica gel
  4. washeluted with 40 and 50% ethyl acetate in hexanes
  5. customHPLC (60/40) 5.13 minutes (>99%)

Sources & evidence

ORD record
ord-1adb39a1fea7461eadb585c9aaf153ee
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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