Trifluoroacetic acid → HCID 67628062, compound

HRID 1599479Notes

Reaction equation

HRID 1599479 reaction equation
C(OC([N:8]1[C:25]2[C@:20]([CH3:27])([CH2:21][CH2:22][C:23](=[O:26])[CH:24]=2)[C@@H:19]2[C@H:10]([C@H:11]3[C@@:15]([CH2:17][CH2:18]2)([CH3:16])[CH2:14][C:13](=[O:28])[CH2:12]3)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:16][C@:15]12[CH2:17][CH2:18][C@H:19]3[C@@H:10]([CH2:9][NH:8][C:25]4[C@:20]3([CH3:27])[CH2:21][CH2:22][C:23](=[O:26])[CH:24]=4)[C@@H:11]1[CH2:12][C:13](=[O:28])[CH2:14]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54538851HCID 54538851, compound

Product 1

HCID 67628062HCID 67628062, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-t-butyloxycarbonyl-6-azaandrost-4-ene-3,16-dione (11, R2 =H) (693 mg, 1.79 mmoles) in methylene chloride (12 mL) was added trifluoroacetic acid (3mL) and the mixture stirred at room temperature for 1.75 hours. The mixture was evaporated in vacuo and the residue dissolved in methylene chloride and shaken with 10% NaHCO3. The resulting solid was filtered and dried in a vacuum oven at 60° C. to give (12, R2 =H) as a white solid. NMR (CDCl3): δ 0.98 (s, 3H, 18-Me); 1.36 (s, 3H, 18-Me); 4.88 (s,1H; NH); 5.09 (s, 1H, 4-H).

Workup

  1. customThe mixture was evaporated in vacuo
  2. dissolutionthe residue dissolved in methylene chloride
  3. stirringshaken with 10% NaHCO3
  4. filtrationThe resulting solid was filtered
  5. customdried in a vacuum oven at 60° C.
  6. customto give (12, R2 =H) as a white solid

Sources & evidence

ORD record
ord-f5330be73d0f4bcf888e5116a1a1400d
Source dataset
uspto-grants-1998_04
Patent number
US05741795

Reaction notes

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