p-Toluenesulfonic acid → HCID 70477335, compound

HRID 462439Notes

Reaction equation

HRID 462439 reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:21][C@@:20]2([CH3:22])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[C@H:18]([NH:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:6][C@@H:5]1[OH:34])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:46](OC(=O)C)(=[O:48])[CH3:47]>C(Cl)(Cl)Cl.C(O)C>[C:46]([O:34][C@@H:5]1[C@@H:4]([O:3][CH2:1][CH3:2])[CH2:21][C@@:20]2([CH3:22])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[C@H:18]([NH:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:6]1)(=[O:48])[CH3:47]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 12804638HCID 12804638, compound

Product 1

HCID 70477335HCID 70477335, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

Ethyl 2β-ethoxy-3α-hydroxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate (200 mg) in chloroform (2.15 ml) containing dry toluene-4-sulphonic acid (PTSA; 172 mg) was stirred for 20 min, then treated with acetic anhydride (0.5 ml) and the mixture left for 18 h. The reaction mixture was diluted with ethanol and evaporated. The residue in ethyl acetate was washed with dilute ammonia solution (2×) and water (1×), dried and evaporated to give the title compound as an oil (220 mg), [α]D +25.8° (CHCl3C=1%), νmax 1720 cm-1.

Workup

  1. waitthe mixture left for 18 h
  2. customevaporated
  3. washThe residue in ethyl acetate was washed with dilute ammonia solution (2×) and water (1×)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-cd4332b7c51246bf86301ee6029bda04
Source dataset
uspto-grants-1985_05
Patent number
US04515786

Reaction notes

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