4-Hydroxypyrrolidine → HCID 10179865, compound

HRID 651089Notes

Reaction equation

HRID 651089 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]([NH:19][CH:20]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:21](O)=[O:22])=[O:18])=[CH:11]2>>[CH2:24]([CH:20]([NH:19][C:17]([C:12]1[NH:13][C:14]2[C:10]([CH:11]=1)=[CH:9][C:8]([Cl:7])=[CH:16][CH:15]=2)=[O:18])[C:21]([N:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1)=[O:22])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 982104-HydroxypyrrolidineHCID 155210162-[(5-Chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid

Product 1

HCID 10179865HCID 10179865, compound

Procedure

Racemic3-pyrrolidinol (2.0 mmol) and 2-[(5-chloro-1H-indole-2-carbonyl)-amino]-3phenyl-propionic acid (1 mmol) were coupled according to procedure A (0-25° C. reaction temperature, washing first with acid then base), and the product purified by column chromatography on silica gel eluted with 0.5-16% ethanol in dichloromethane to give a colorless foam: Yield 260 mg, 63%; HPLC (60/40) 100%, 3.86 minutes; PBMS 412/414 (MH+, 100%);

Workup

  1. custom0-25° C. reaction temperature
  2. washwashing first with acid
  3. custombase), and the product purified by column chromatography on silica gel
  4. washeluted with 0.5-16% ethanol in dichloromethane
  5. customto give a colorless foam

Sources & evidence

ORD record
ord-fead3c36e76f420f8ee6b38a427c36cc
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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