Ethanol → HCID 70418099, compound

HRID 2231294Notes

Reaction equation

HRID 2231294 reaction equation
C[O:2][C:3](=[O:28])[CH:4]([C@@:6]1([CH2:26][CH3:27])[C@@H:15]2[N:10]([CH2:11][CH2:12][C:13]3[C:22]4[C:17](=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][CH:21]=4)[NH:16][C:14]=32)[CH2:9][CH2:8][CH2:7]1)[CH3:5].[OH-].[K+].C(O)C>>[CH2:26]([C@:6]1([CH:4]([CH3:5])[C:3]([OH:28])=[O:2])[C@@H:15]2[N:10]([CH2:11][CH2:12][C:13]3[C:22]4[C:17](=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][CH:21]=4)[NH:16][C:14]=32)[CH2:9][CH2:8][CH2:7]1)[CH3:27]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 70417320HCID 70417320, compound

Product 1

HCID 70418099HCID 70418099, compoundYield 81%

Procedure

A solution containing 0.385 g (0.001 mole) of (-)-(1S,12bS)-1d-ethyl-10-nitro-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-1-yl-propionic acid methyl ester (prepared as described in Example 53) dissolved in the mixture of 0.169 g. (0.003 moles) of potassium hydroxide in 8 moles of 96% ethanol is refluxed for 20 minutes, then evaporated. The residue is dissolved in a little amount of water and acidified to pH 6 by adding acetic acid. The precipitate is filtered, washed with water and dried to give 0.300 g. (81% yield) of the title compound which can be used without purification for the preparation of the acid amide.

Workup

  1. dissolutiondissolved in the mixture of 0.169 g
  2. customevaporated
  3. dissolutionThe residue is dissolved in a little amount of water
  4. additionby adding acetic acid
  5. filtrationThe precipitate is filtered
  6. washwashed with water
  7. customdried
  8. customto give 0.300 g

Sources & evidence

ORD record
ord-f6b95592edcd447e958641a7911a8734
Source dataset
uspto-grants-1988_11
Patent number
US04782052

Reaction notes

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