Water → 7-Hydroxy-pregna-1,4-dien-3-one-20-carbaldehyde

HRID 1196309Notes

Reaction equation

HRID 1196309 reaction equation
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:28])[CH2:13][CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][C@@H:17](O)[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3]CC(O)=O.[OH-:29].[Na+].[OH2:31]>>[OH:29][C@@H:17]1[CH2:18][C:19]2[C@:20]([CH3:26])([CH:21]=[CH:22][C:23](=[O:25])[CH:24]=2)[C@@H:15]2[C@@H:16]1[C@H:11]1[C@:12]([CH3:28])([CH2:13][CH2:14]2)[C@@H:8]([CH:2]([CH:3]=[O:31])[CH3:1])[CH2:9][CH2:10]1

Participants

4

Reactant 3

HCID 962WaterHCID 10133Chenodeoxycholic AcidHCID 14798Sodium Hydroxide2×

Product 1

HCID 228438847-Hydroxy-pregna-1,4-dien-3-one-20-carbaldehyde

Procedure

The cultivation procedure of Example 1 was repeated except that chenodeoxycholic acid was used in an amount of 1.0 g instead of 2.0 g, that sodium hydroxide was used in an amount of 0.1 g instead of 0.2 g and that the cultivation time was 1 day instead of 2 days. The resulting culture broth was adjusted to pH 9.0 with 1N-aqueous sodium hydroxide solution and centrifuged to separate the cells and the precipitate formed in the course of culture from the supernatant. The precipitate and cells were mixed with 50 ml of water and the mixture was centrifuged to separate the aqueous layer from the insoluble fraction. The insoluble fraction was mixed with 200 ml of methanol and the mixture was centrifuged to separate the cells from the methanol layer. The methanol layer was diluted with 10 ml of water and the methanol was distilled off under reduced pressure. The resulting precipitate was recovered by filtration and dried to give 0.77 g of 7α-hydroxypregna-1,4-dien-3-one-20 -carbaldehyde. Determined by high performance liquid chromatography, this product had a purity of 95.1%.

Workup

  1. customto separate the cells
  2. customthe precipitate formed in the course of culture from the supernatant
  3. customto separate the aqueous layer from the insoluble fraction
  4. additionThe insoluble fraction was mixed with 200 ml of methanol
  5. customto separate the cells from the methanol layer
  6. additionThe methanol layer was diluted with 10 ml of water
  7. distillationthe methanol was distilled off under reduced pressure
  8. filtrationThe resulting precipitate was recovered by filtration
  9. customdried

Sources & evidence

ORD record
ord-122b11ad53754ca6aa3325350711d4de
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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