Sodium Hydroxide → HCID 86739910, compound

HRID 615186Notes

Reaction equation

HRID 615186 reaction equation
[Cl:1][C:2]([Cl:32])([Cl:31])[CH2:3][O:4][C:5]([NH:7][C@@H:8]1[CH2:25][C@@:23]2([CH3:24])[C@@H:19]([CH2:20][CH2:21][C@@H:22]2[C:26]([O:28][CH3:29])=[O:27])[C@H:18]2[C@H:9]1[C@:10]1([CH3:30])[C@@H:15]([CH2:16][CH2:17]2)[CH2:14][CH:13]=[CH:12][CH2:11]1)=[O:6].BrCC(N)=[O:36].Cl(O)(=O)(=O)=O.[OH-].[Na+]>O1CCCC1.O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].CO>[O:36]1[C@@H:13]2[CH2:14][C@H:15]3[C@:10]([CH3:30])([CH2:11][C@H:12]12)[C@@H:9]1[C@H:18]([C@H:19]2[C@@:23]([CH2:25][C@H:8]1[NH:7][C:5]([O:4][CH2:3][C:2]([Cl:31])([Cl:32])[Cl:1])=[O:6])([CH3:24])[C@@H:22]([C:26]([O:28][CH3:29])=[O:27])[CH2:21][CH2:20]2)[CH2:17][CH2:16]3

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 696322-BromoacetamideHCID 12804687HCID 12804687, compound

Product 1

HCID 86739910HCID 86739910, compoundYield 17.2%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 656671Sodium PyrosulfiteSolvent

Procedure

Methyl 11α-(2,2,2-trichloroethoxycarbonylamino)5α-androst-2-ene-17β-carboxylate (507 mg) in tetrahydrofuran (15 ml) and water (7.5 ml) was treated with N bromoacetamide (193 mg) and 60% perchloric acid (0.15 ml) and stirred at room temperature for 30 minutes. The reaction mixture was diluted with 5% sodium metabisulphite solution (30 ml) and water (50 ml). The suspension was extracted with ether (3×). The ether extracts were washed with water, dried and evaporated to give a foam. This was dissolved in methanol (50 ml), treated with 2M sodium hydroxide solution (10 ml), and stirred at room temperature for 30 minutes. The solution was concentrated by evaporation, diluted with water (100 ml) and extracted with ethyl acetate (3×). The extracts were washed with water (1×), dried and evaporated to give a white foam. This was purified by preparative t.l.c. in ethyl acetate/petrol (1:2) and crystallised from ether to give the title compound (90 mg) m.p. 153°-155° C., [α]D +25.2°.

Workup

  1. extractionThe suspension was extracted with ether (3×)
  2. washThe ether extracts were washed with water
  3. customdried
  4. customevaporated
  5. customto give a foam
  6. stirringstirred at room temperature for 30 minutes
  7. concentrationThe solution was concentrated by evaporation
  8. additiondiluted with water (100 ml)
  9. extractionextracted with ethyl acetate (3×)
  10. washThe extracts were washed with water (1×)
  11. customdried
  12. customevaporated
  13. customto give a white foam
  14. customThis was purified by preparative t.l.c
  15. customin ethyl acetate/petrol (1:2) and crystallised from ether

Sources & evidence

ORD record
ord-b397aa5107f44a7b90e3664c521ac92b
Source dataset
uspto-grants-1985_02
Patent number
US04497805

Reaction notes

Loading…