Lithium Hydroxide → (2S)-2-[(1,2,3,3a,4,8b-Hexahydrocyclopenta[b]Indol-5-ylcarbonyl)Amino]-Propanoic Acid

HRID 2227737Notes

Reaction equation

HRID 2227737 reaction equation
[OH-].[Li+].[CH2:3]1[CH:14]2[CH:6]([NH:7][C:8]3[C:9]([C:15]([NH:17][C@@H:18]([CH3:24])[C:19]([O:21]CC)=[O:20])=[O:16])=[CH:10][CH:11]=[CH:12][C:13]=32)[CH2:5][CH2:4]1>C1COCC1>[CH2:3]1[CH:14]2[CH:6]([NH:7][C:8]3[C:9]([C:15]([NH:17][C@@H:18]([CH3:24])[C:19]([OH:21])=[O:20])=[O:16])=[CH:10][CH:11]=[CH:12][C:13]=32)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 12132976ethyl (2S)-2-[(1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-5-ylcarbonyl)amino]propanoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1 M aqueous lithium hydroxide solution (13 mmol, 13 mL) was added to a solution of ethyl (2S)-2-[(1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-5-ylcarbonyl)amino]propanoate (6.1 mmol, 1.9 g) in THF (50 mL). The reaction mixture was stirred at room temperature for 18 h. The reaction was concentrated in vacuo and diluted with 0.1 N HCI and ethyl acetate. The phases were separated and the organic phase was washed with water, dried over MgSO4, filtered, and concentrated to give a yellow oil (1.6 g, 6.1 mmol, quantitative).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with 0.1 N HCI and ethyl acetate
  3. customThe phases were separated
  4. washthe organic phase was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow oil (1.6 g, 6.1 mmol, quantitative)

Sources & evidence

ORD record
ord-fe01335f4ef549cb87548266efb314de
Source dataset
uspto-grants-2002_07
Patent number
US06414144B1

Reaction notes

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