p-Toluenesulfonic acid → HCID 70477819, compound

HRID 462442Notes

Reaction equation

HRID 462442 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][C@@:21]2([CH3:23])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:20]2[C@H:19]([NH:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C:31]([O:33][CH3:34])=[O:32])[CH2:7][C@@H:6]1[OH:35])(=[O:3])[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.[C:47](OC(=O)C)(=[O:49])[CH3:48]>C(Cl)(Cl)Cl.C(O)C.C(OCC)(=O)C>[CH:25]1([NH:24][C@@H:19]2[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C:31]([O:33][CH3:34])=[O:32])[C@H:11]3[C@H:20]2[C@:21]2([CH3:23])[C@@H:8]([CH2:9][CH2:10]3)[CH2:7][C@H:6]([O:35][C:47](=[O:49])[CH3:48])[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:22]2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

7

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 12804671HCID 12804671, compound

Product 1

HCID 70477819HCID 70477819, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2β-acetoxy-11α-cyclohexylamino-3α-hydroxy-5α-androstane-17β-carboxylate (1.156 g) in chloroform (12.5 ml) containing dry PTSA (1.0 g) was stirred for 20 min. then treated with acetic anhydride (2.9 ml) and the mixture left for 18 h. The mixture was diluted with ethanol and evaporated to give an oil. This was dissolved in ethyl acetate, and washed with dilute ammonia solution (1×) water (1×), dried and evaporated under reduced pressure to give a foam. This was purified by preparative t.l.c. in chloroform/methanol (9:1) to give the title compound (790 mg), [α]D +36.8°, νmax 1724 cm-1.

Workup

  1. waitthe mixture left for 18 h
  2. customevaporated
  3. customto give an oil
  4. washwashed with dilute ammonia solution (1×) water (1×)
  5. customdried
  6. customevaporated under reduced pressure
  7. customto give a foam
  8. customThis was purified by preparative t.l.c

Sources & evidence

ORD record
ord-4967ee0b114941dea3a5f406337fe068
Source dataset
uspto-grants-1985_05
Patent number
US04515786

Reaction notes

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