Sodium Hydroxide → HCID 8032838, compound

HRID 2195603Notes

Reaction equation

HRID 2195603 reaction equation
[CH2:1]([N:8]1[CH2:16][CH2:15][CH2:14][CH:10]([C:11]([NH2:13])=[O:12])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>>[CH2:1]([N:8]1[CH2:16][CH2:15][CH2:14][C@@H:10]([C:11]([NH2:13])=[O:12])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Procedure

Cupriavidus sp. KNK-J915 stain (FERN BP-10739) was inoculated in a medium (glycerol 1.0%, peptone 0.5%, malt extract 0.3%, yeast extract 0.3%, isovaleronitrile 0.1%, pH 7.0) sterilized in a Sakaguchi flask, and stirred and cultivated at 30° C. for 72 hours. After completion of the cultivation, the bacterial cells were collected by centrifugal separation, and suspended in 100 mM phosphate buffer (pH 7.0) to obtain a 20-fold concentrated bacterial cell suspension. To the bacterial cell suspension (100 ml), racemic 1-benzylnipecotamide (5 g) was added. The pH of the solution was adjusted to 7 using NaOH, and then the mixture was shaken at 30° C. for 60 hours. After completion of the reaction, solid substance such as bacterial cells was removed by centrifugal separation from the reaction mixture, and the pH of the mixture was adjusted to 10.0 using NaOH. The mixture was stirred at room temperature for 1 hour, and then precipitated crystal was filtrated to obtain 2.4 g of (R)-1-benzylnipecotamide. The compound was analyzed by the method of Example 1; as a result, the optical purity was 99.8% ee.

Workup

  1. extractionKNK-J915 stain (FERN BP-10739) was inoculated in a medium (glycerol 1.0%, peptone 0.5%, malt extract 0.3%, yeast extract 0.3%, isovaleronitrile 0.1%, pH 7.0)
  2. customAfter completion of the cultivation, the bacterial cells were collected by centrifugal separation
  3. customto obtain a 20-fold concentrated bacterial cell suspension
  4. stirringthe mixture was shaken at 30° C. for 60 hours
  5. customAfter completion of the reaction, solid substance such as bacterial cells
  6. customwas removed by centrifugal separation from the reaction mixture
  7. stirringThe mixture was stirred at room temperature for 1 hour
  8. customprecipitated crystal
  9. filtrationwas filtrated

Sources & evidence

ORD record
ord-59cc5aa8fc3b447c929d5b5e2caebde3
Source dataset
uspto-grants-2012_12
Patent number
US08338142B2

Reaction notes

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