3-Oxo-4-aza-5-androstene-17beta-carboxylic acid → (4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid

HRID 1007558

反応式

HRID 1007558 の反応式
[O:1]=[C:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:21]([OH:23])=[O:22])[NH:3]1.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:13][C@@:12]12[C@@H:11]([C:21]([OH:23])=[O:22])[CH2:10][CH2:9][C@H:8]1[C@@H:7]1[CH2:6][CH2:5][C@H:4]3[NH:3][C:2](=[O:1])[CH2:19][CH2:18][C@:17]3([CH3:20])[C@H:16]1[CH2:15][CH2:14]2

参加物

4

反応物 2

HCID 4754473-Oxo-4-aza-5-androstene-17beta-carboxylic acidHCID 517165Ammonium Acetate

生成物 1

HCID 9818495(4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

The hydrogenation vessel was charged with acetic acid (530 l), 3-oxo-4-aza-5-androstene-17β-carboxylic acid 2 (33.5 kg.), and ammonium acetate (1.0 kg, 0.1 eq.). After purging at 20-25° C. with nitrogen, the platinum oxide catalyst (3.0 kg.) was charged, the stirrer started and the temperature adjusted to 20-25° C. After purging with hydrogen, the stirring batch was allowed to take up hydrogen. After 30 minutes at ≦30° C., the temperature was adjusted to 60-65° C., and stirring continued until hydrogen uptake ceased. After purging with nitrogen, Solka Floc (1.7 kg.) was charged, and the hot reaction mixture recirculated through a filter until the solution was clear. The hot reaction filtrate was transferred to a clean vessel. The reactor was rinsed with hot acetic acid (100 l.), and the rinse was recirculated as a wash through the filter. The combined filtrates/wash were distilled under vacuum at ≦70° C. to about 3.6 volumes. The resulting slurry was cooled to ≦25° C. Methanol (130 l.) was added and the mixture stirred for at least 2 hours at ≦25° C. The product was collected by filtration; the cake washed with methanol and dried in vacuo at ≦60° C. Weight range: 25-28.5 kg (75-85% theory, 75-85% w/w).

後処理

  1. customAfter purging at 20-25° C. with nitrogen
  2. additionthe platinum oxide catalyst (3.0 kg.) was charged
  3. customadjusted to 20-25° C
  4. customAfter purging with hydrogen
  5. customwas adjusted to 60-65° C.
  6. customAfter purging with nitrogen, Solka Floc (1.7 kg.)
  7. additionwas charged
  8. filtrationa filter until the solution
  9. customThe hot reaction filtrate was transferred to a clean vessel
  10. washThe reactor was rinsed with hot acetic acid (100 l.)
  11. washa wash through the filter
  12. washThe combined filtrates/wash
  13. distillationwere distilled under vacuum at ≦70° C. to about 3.6 volumes
  14. temperatureThe resulting slurry was cooled to ≦25° C
  15. additionMethanol (130 l.) was added
  16. stirringthe mixture stirred for at least 2 hours at ≦25° C
  17. filtrationThe product was collected by filtration
  18. washthe cake washed with methanol
  19. customdried in vacuo at ≦60° C

出典と根拠

ORDレコード
ord-b35a157c977a4e18a932d67c2e5c1504
出典データセット
uspto-grants-2004_09
特許番号
US06794508B2

関連ノート

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