Potassium Hydroxide → HCID 10681252, compound

HRID 380281Notes

Reaction equation

HRID 380281 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:18])[CH2:6][CH:7]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:17])[CH:14]=2)[O:9][CH2:8]1)[CH3:3].[OH-].[K+]>C1(C)C=CC=CC=1>[CH2:2]([O:4][C:5](=[O:18])[CH2:6][CH:7]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:17])[CH:14]=2)[O:9][CH2:8]1)[CH3:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69822895HCID 69822895, compound

Product 1

HCID 10681252HCID 10681252, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 10 ml of a sterilized medium (pH 7.4) containing 0.1% yeast extract, 0.1% meat extract (Ehrlich), 0.2% NZ amine (TYPE 1), 0.5% sodium chloride, 0.05% potassium dihydrogenphosphate, 0.1% dipotassium hydrogenphosphate, 0.01% magnesium sulfate, and 1.0% soluble starch was inoculated 5% culture of Pseudonocardia thermophila FERM BP-6275 which had been preliminary cultured in the same buffer. The culture was carried out at 52° C. for 72 hours. Wet cells obtained by centrifugation were added to 50 ml of a reaction solution (pH 8.0, adjusted with potassium hydroxide) containing 1 g of racemic 6-aminochroman-3-acetic acid ethyl ester hydrochloride. Hydrolytic reaction was carried out at 55° C. for 6 hours while maintaining the pH at 8.0 with a 2% potassium hydroxide solution. After the reaction, 20 ml of toluene were added and unreacted 6-aminochroman-3-acetic acid ethyl ester was extracted. Most of the remaining 6-aminochroman-3-acetic acid ethyl ester was extracted into the toluene layer and hydrolyzed 6-aminochroman-3-acetic acid was retained in the water layer. (S) 6-aminochroman-3-acetic acid ethyl ester with a purity of more than 99% was obtained by concentrating the toluene layer (yield: 35%).

Workup

  1. additionTo 10 ml of a sterilized medium (pH 7.4) containing 0.1% yeast
  2. extractionextract
  3. extraction0.1% meat extract (Ehrlich), 0.2% NZ amine (TYPE 1), 0.5% sodium chloride, 0.05% potassium dihydrogenphosphate, 0.1% dipotassium hydrogenphosphate, 0.01% magnesium sulfate, and 1.0% soluble starch
  4. customWet cells obtained by centrifugation
  5. customHydrolytic reaction
  6. waitwas carried out at 55° C. for 6 hours
  7. additionwere added
  8. extractionunreacted 6-aminochroman-3-acetic acid ethyl ester was extracted
  9. extractionMost of the remaining 6-aminochroman-3-acetic acid ethyl ester was extracted into the toluene layer and hydrolyzed 6-aminochroman-3-acetic acid

Sources & evidence

ORD record
ord-749a6580191846bd96604f708c69ef8d
Source dataset
uspto-grants-2001_10
Patent number
US06303349B1

Reaction notes

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