Propionic anhydride → 35775-84-9

HRID 466507Notes

Reaction equation

HRID 466507 reaction equation
[CH3:1][CH2:2][C:3]([O:5][CH:6]1[CH:23]([O:24][CH3:25])[CH:22]([O:26][CH:27]2[O:32][CH:31]([CH3:33])[CH:30]([O:34][CH:35]3[O:40][CH:39]([CH3:41])[CH:38]([O:42][C:43]([CH2:45][CH3:46])=[O:44])[C:37]([OH:48])([CH3:47])[CH2:36]3)[CH:29]([N:49]([CH3:51])[CH3:50])[CH:28]2[OH:52])[CH:21]([CH2:53][CH:54]=[O:55])[CH2:20][CH:19]([CH3:56])[CH:18]([OH:57])[CH:17]=[CH:16][CH:14]2[O:15][CH:13]2[CH2:12][CH:11]([CH3:58])[O:10][C:8](=[O:9])[CH2:7]1)=[O:4].[CH2:59](O)[C:60](N)(CO)[CH2:61][OH:62].C([O-])(=O)/C=C\C([O-])=O.C(OC(=O)CC)(=O)CC>C(C(C)=O)C(C)C>[CH3:1][CH2:2][C:3]([O:5][CH:6]1[CH:23]([O:24][CH3:25])[CH:22]([O:26][CH:27]2[O:32][CH:31]([CH3:33])[CH:30]([O:34][CH:35]3[O:40][CH:39]([CH3:41])[CH:38]([O:42][C:43]([CH2:45][CH3:46])=[O:44])[C:37]([OH:48])([CH3:47])[CH2:36]3)[CH:29]([N:49]([CH3:50])[CH3:51])[CH:28]2[OH:52])[CH:21]([CH2:53][CH:54]=[O:55])[CH2:20][CH:19]([CH3:56])[CH:18]([O:57][C:61]([CH2:60][CH3:59])=[O:62])[CH:17]=[CH:16][CH:14]2[O:15][CH:13]2[CH2:12][CH:11]([CH3:58])[O:10][C:8](=[O:9])[CH2:7]1)=[O:4]

Participants

5

Reactant 3

HCID 31263Propionic anhydrideHCID 643604535775-82-7HCID 86757951HCID 86757951, compound

Product 1

HCID 644543435775-84-9

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
28 °C

Procedure

A 10 l-capacity galss-linked reaction vessel (with stirrer) was charged with 2 l of methyl isobutyl ketone warmed at 28° C. in advance, in which was dissolved 10 g of maridomycin III. To the solution was then added 2 l of a tris(hydroxymethyl)aminomethane-maleate buffer solution (0.2M. pH 7.0) dissolving 500 mg of carboxyl esterase obtained in Reference Example 1. To the solvent layer was added 20 ml of propionic anhydride, and the reaction was allowed to proceed for one hour under stirring. The reaction solution was shifted to a 10 l capacity separating funnel, and thus the aqueous phase was removed. To the remainder was added 500 ml of an aqueous solution of sodium bicarbonate (2%) (w/v). The mixture was sufficiently stirred, followed by removing the aqueous portion. Washing with an aqueous solution of sodium bicarbonate was repeated once more, followed by washing with 2 l of distilled water twice in the separating funnel. The organic phase was shifted to a 3 l-capacity conical flask, to which was added 100 g of anhydrous sodium sulfate, and the mixture was left standing for two hours. The anhydrous sodium sulfate was filtered off by using filter paper, and the reaction solution was concentrated to dryness to obtain 10 g of 9-propionyl maridomycin III as crude crystals.

Workup

  1. dissolutiondissolving 500 mg of carboxyl esterase
  2. customobtained in Reference Example 1
  3. customseparating funnel
  4. customthus the aqueous phase was removed
  5. additionTo the remainder was added 500 ml of an aqueous solution of sodium bicarbonate (2%) (w/v)
  6. stirringThe mixture was sufficiently stirred
  7. customby removing the aqueous portion
  8. washWashing with an aqueous solution of sodium bicarbonate
  9. washby washing with 2 l of distilled water twice in the separating funnel
  10. additionwas added 100 g of anhydrous sodium sulfate
  11. waitthe mixture was left
  12. waitstanding for two hours
  13. filtrationThe anhydrous sodium sulfate was filtered off
  14. filtrationby using filter paper
  15. concentrationthe reaction solution was concentrated to dryness

Sources & evidence

ORD record
ord-b4642096ac854093ba8086b584a6824c
Source dataset
uspto-grants-1992_10
Patent number
US05156962

Reaction notes

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