HCID 12132982, compound → HCID 12132983, compound

HRID 1836098Notes

Reaction equation

HRID 1836098 reaction equation
[CH2:1]1[CH:12]2[CH:4]([NH:5][C:6]3[C:7]([C:13]([NH:15][C@@H:16]([CH2:20][OH:21])[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>[OH:18][CH2:17][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:20]1=[O:21]

Participants

3

Reactant 1

HCID 12132982HCID 12132982, compound

Product 1

HCID 12132983HCID 12132983, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure of method 7E, (2S)-2-[(1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-5-ylcarbonyl)amino]-3-hydroxypropanoic acid (1.5 mmol, 430 mg) was cyclized by refluxing in acetic acid (40 mL). Purification by flash chromatography through silica gel (elution with 5% methanol-chloroform) provided each diastereomer: less polar product (0.55 mmol, 0.15 g, 37%) arbitrarily assigned as the R,R configuration and more polar product (0.26 mmol, 0.070 g, 17%) 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-7f1a2db6f9634f0d870584ea237fcf73
Source dataset
uspto-grants-2004_08
Patent number
US06777407B2

Reaction notes

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