Phosphate → ethyl 2-[(1R)-1-hydroxyethyl]acrylate

HRID 2255672Notes

Reaction equation

HRID 2255672 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C(=O)([O-])[O-].[Ca+2].P([O-])([O-])([O-])=O.C([O:26][CH:27]([C:29](=[CH2:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:28])(=O)C>>[OH:26][C@@H:27]([C:29](=[CH2:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:28]

Participants

5

Conditions

Temperature
30 °C

Procedure

A loopful of slant culture of Bacillus megaterium No. 1253 was inoculated to a medium (80 ml) containing bouillon 1%, glucose 1% and calcium carbonate 0.2%. The flash was incubated with shaking for 24 hours at 30° C. The resultant seed culture (1.6 ml) was inoculated to the same medium (80 ml) and cultured for 2 days at 30° C. Eighty (80) ml of this cultured broth, 3 ml of 1M phosphate buffer (pH 7.5) and 1 g of ethyl 2-(1-acetoxyethyl)acrylate were poured into a 250 ml wide-mouth flask and incubated for 20 hours at 30° C. with shaking. The whole mixture was extracted twice with 40 ml of ethyl acetate and the combined extract was dried. After removal of the solvent in vacuo, the crude material was applied on a silica gel column and developed with a mixture of n-hexane and ethyl acetate (4:1). The fractions containing the desired compounds were collected and dried in vacuo to give 250 mg of ethyl 2-[(1R)-1-hydroxyethyl]acrylate.

Workup

  1. waitcultured for 2 days at 30° C
  2. waitincubated for 20 hours at 30° C.
  3. stirringwith shaking
  4. extractionThe whole mixture was extracted twice with 40 ml of ethyl acetate
  5. extractionthe combined extract
  6. customwas dried
  7. customAfter removal of the solvent in vacuo
  8. additiondeveloped with a mixture of n-hexane and ethyl acetate (4:1)
  9. additionThe fractions containing the desired compounds
  10. customwere collected
  11. customdried in vacuo

Sources & evidence

ORD record
ord-3ff8d090148d4ddea3dc236222c48974
Source dataset
uspto-grants-1993_08
Patent number
US05241064

Reaction notes

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