HCID 69263394, compound → HCID 12132978, compound

HRID 916616Notes

Reaction equation

HRID 916616 reaction equation
[CH2:1]1[CH:12]2[CH:4]([NH:5][C:6]3[C:7]([C:13]([NH:15][C@H:16]([CH3:20])[C:17](O)=[O:18])=[O:14])=[CH:8][CH:9]=[CH:10][C:11]=32)[CH2:3][CH2:2]1>C(O)(=O)C>[CH3:20][C@H:16]1[NH:15][C:13](=[O:14])[C:7]2=[C:6]3[C:11](=[CH:10][CH:9]=[CH:8]2)[CH:12]2[CH2:1][CH2:2][CH2:3][CH:4]2[N:5]3[C:17]1=[O:18]

Participants

3

Reactant 1

HCID 69263394HCID 69263394, compound

Product 1

HCID 12132978HCID 12132978, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure of method 7E, (2R)-2-[(1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-5-ylcarbonyl)amino]propanoic acid was cyclized by refluxing in acetic acid (50 mL). Purification by flash chromatography through silica gel (elution with 5% methanol-chloroform) provided each diastereomer: less polar product (1.5 mmol, 0.39 g, 56% over 2 steps) arbitrarily assigned as the R,R configuration and more polar product (0.47 mmol, 0.11 g, 17% over 2 steps) assigned as the S,S configuration.

Workup

  1. customPurification by flash chromatography through silica gel (elution with 5% methanol-chloroform)
  2. customprovided each diastereomer

Sources & evidence

ORD record
ord-1f1c46008a5748949d9a584397913285
Source dataset
uspto-grants-2007_09
Patent number
US07271163B2

Reaction notes

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