(2S)-2-[(1,2,3,3a,4,8b-Hexahydrocyclopenta[b]Indol-5-ylcarbonyl)Amino]-Propanoic Acid → (2S)-2-Methyl-2,3,8,9,10,10a-Hexahydro-7bH-Cyclopenta[b][1,4]Diazepino-[6,7,1-hi]Indole-1,4-Dione

HRID 916613Notes

Reaction equation

HRID 916613 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 12132977(2S)-2-[(1,2,3,3a,4,8b-Hexahydrocyclopenta[b]Indol-5-ylcarbonyl)Amino]-Propanoic Acid

Product 1

HCID 69263029(2S)-2-Methyl-2,3,8,9,10,10a-Hexahydro-7bH-Cyclopenta[b][1,4]Diazepino-[6,7,1-hi]Indole-1,4-DioneYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (2S)-2-[(1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-5-ylcarbonyl)amino]propanoic acid (6.1 mmol, 1.6 g) was dissolved in acetic acid (50 mL) and heated to reflux for 18 h. The reaction was allowed to cool to room temperature and was concentrated to dryness. The crude material was purified by flash column chromatography (silica gel; 1:1 ethyl acetate-hexanes) to provide two diastereomers: less polar product (0.88 mmol, 0.23 g, 14%) and more polar product (0.18 mmol, 45 mg, 3%). The mixed fractions were also collected to provide another 3.9 mmol (1.0 g, 64%) of material.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 h
  3. concentrationwas concentrated to dryness
  4. customThe crude material was purified by flash column chromatography (silica gel; 1:1 ethyl acetate-hexanes)
  5. customto provide two diastereomers
  6. customThe mixed fractions were also collected

Sources & evidence

ORD record
ord-7de1338d83e84513bcd73c247cc8397a
Source dataset
uspto-grants-2007_09
Patent number
US07271163B2

Reaction notes

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