p-Toluenesulfonic acid → HCID 70478769, compound

HRID 462443Notes

Reaction equation

HRID 462443 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][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C:30]([O:32][CH3:33])=[O:31])[CH2:7][C@@H:6]1[OH:34])(=[O:3])[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.[C:46](OC(=O)C)(=[O:48])[CH3:47]>C(Cl)(Cl)Cl.C(O)C.C(OCC)(=O)C>[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][CH2:25][CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C:30]([O:32][CH3:33])=[O:31])[CH2:7][C@@H:6]1[O:34][C:46](=[O:48])[CH3:47])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 12804669HCID 12804669, compound

Product 1

HCID 70478769HCID 70478769, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2β-acetoxy-3α-hydroxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate (3.069 g) in chloroform (33 ml) containing dry PTSA (2.64 g) was stirred for 20 min then treated with acetic anhydride (6.5 ml) and the mixture left for 5 h. The mixture was diluted with ethanol and evaporated to give an oil. This was dissolved in ethyl acetate, washed with aqueous ammonia solution (2×) and water (1×), dried and evaporated to give an oil (2.867 g). This was purified by preparative t.l.c. in chloroform/methanol (9:1) to give the title compound [α]D +48.6°, νmax 1730 cm-1.

Workup

  1. waitthe mixture left for 5 h
  2. customevaporated
  3. customto give an oil
  4. washwashed with aqueous ammonia solution (2×) and water (1×)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-1f9f2fd8bbe14936b6a2b4d7689ccc8a
Source dataset
uspto-grants-1985_05
Patent number
US04515786

Reaction notes

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