Sodium Hydroxide → HCID 86739911, compound

HRID 615188Notes

Reaction equation

HRID 615188 reaction equation
[CH3:1][CH:2]([CH3:29])[CH2:3][CH2:4][NH:5][C@@H:6]1[CH2:23][C@@:21]2([CH3:22])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:24]([O:26][CH3:27])=[O:25])[C@H:16]2[C@H:7]1[C@:8]1([CH3:28])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][CH:11]=[CH:10][CH2:9]1.BrCC(N)=[O:33].Cl(O)(=O)(=O)=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>O1CCCC1.O.Cl.CO>[O:33]1[C@@H:11]2[CH2:12][C@H:13]3[C@:8]([CH3:28])([CH2:9][C@H:10]12)[C@@H:7]1[C@H:16]([C@H:17]2[C@@:21]([CH2:23][C@H:6]1[NH:5][CH2:4][CH2:3][CH:2]([CH3:29])[CH3:1])([CH3:22])[C@@H:20]([C:24]([O:26][CH3:27])=[O:25])[CH2:19][CH2:18]2)[CH2:15][CH2:14]3

Participants

10

Reactant 5

HCID 14798Sodium Hydroxide2×HCID 24247Perchloric AcidHCID 696322-BromoacetamideHCID 656671Sodium PyrosulfiteHCID 18595991HCID 18595991, compound

Product 1

HCID 86739911HCID 86739911, compoundYield 44.1%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 11α-(3-methylbutylamino)-5α-androst-2-ene-17β-carboxylate (403 mg) in tetrahydrofuran (15 ml), water (7 ml) and 2M hydrochloric acid (0.5 ml) was treated with N bromoacetamide (193 mg) and 60% perchloric acid (0.15 ml) and stirred for 30 min. 5% sodium metabisulphite (30 ml) was added and the resulting solution diluted with water and brought to pH 11 with 2M sodium hydroxide solution. This was extracted with ether and the ether extracts were washed with water, dried and evaporated to give an oil. This was dissolved in methanol (50 ml), treated with 2M sodium hydroxide (10 ml) and stirred for 30 min. The solution was concentrated by evaporation, diluted with water (100 ml) and extracted with ethyl acetate (3×). The extracts were washed with water, dried and evaporated to give an oil. This was purified by preparative t.l.c. in ethyl acetate to give the title compound (185 mg), [α]D +33.6°.

Workup

  1. extractionThis was extracted with ether
  2. washthe ether extracts were washed with water
  3. customdried
  4. customevaporated
  5. customto give an oil
  6. stirringstirred for 30 min
  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
  11. customdried
  12. customevaporated
  13. customto give an oil
  14. customThis was purified by preparative t.l.c

Sources & evidence

ORD record
ord-705faa256edd49bebc0ae227b1349286
Source dataset
uspto-grants-1985_02
Patent number
US04497805

Reaction notes

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