Ethyl formate → HCID 12961935, compound

HRID 1065687Notes

Reaction equation

HRID 1065687 reaction equation
[Na].[CH2:2]1[O:26][C:5]2([CH2:22][CH2:21][C@@:20]3([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@@H:19]3[CH2:18][CH2:17][C@@:15]3([CH3:16])[C@H:11]4[CH2:12][C@H:13]([OH:25])[C@H:14]3[NH2:24])[CH2:6]2)[O:4][CH2:3]1.[CH:27](OCC)=[O:28]>C(O)C>[CH2:3]1[O:4][C:5]2([CH2:22][CH2:21][C@@:20]3([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@@H:19]3[CH2:18][CH2:17][C@@:15]3([CH3:16])[C@H:11]4[CH2:12][C@H:13]([OH:25])[C@H:14]3[NH:24][CH:27]=[O:28])[CH2:6]2)[O:26][CH2:2]1

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 5360545SodiumHCID 12961933HCID 12961933, compound

Product 1

HCID 12961935HCID 12961935, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.37 g) was added to a stirred suspension of 17α-amino-16β-hydroxy-5α-androstan-3-one ethylene acetal (5.5 g) in ethyl formate (55 ml) and ethanol (27.5 ml) and the stirred mixture was heated under reflux for 11/2 h. After removal of the solvent, the residue was dissolved in chloroform and the solution was washed with water and dried (MgSO4). Evaporation of the solvent and crystallisation of the product from chloroform-ethyl acetate gave 17α-formamido-16β-hydroxy-5α-androstan-3-one ethylene acetal (4.5 g). A second recrystallisation furnished an analytical sample m.p. 277°-280° C., [α]DDMSO +58° (C 1.0).

Workup

  1. temperaturethe stirred mixture was heated
  2. temperatureunder reflux for 11/2 h
  3. customAfter removal of the solvent
  4. dissolutionthe residue was dissolved in chloroform
  5. washthe solution was washed with water
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent and crystallisation of the product from chloroform-ethyl acetate

Sources & evidence

ORD record
ord-b336817ce95146adb84e2508fc75b420
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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