p-Toluenesulfonic acid → HCID 70477498, compound

HRID 462444Notes

Reaction equation

HRID 462444 reaction equation
[CH:1]1([NH:7][C@@H:8]2[CH2:25][C@@:23]3([CH3:24])[C@@H:19]([CH2:20][CH2:21][C@@H:22]3[C:26]([O:28][CH3:29])=[O:27])[C@H:18]3[C@H:9]2[C@:10]2([CH3:31])[C@@H:15]([CH2:16][CH2:17]3)[CH2:14][C@H:13]([OH:30])[CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.[C:43](OC(=O)C)(=[O:45])[CH3:44]>C(Cl)(Cl)Cl.C(O)C.C([O-])(O)=O.[Na+].O>[C:43]([O:30][C@@H:13]1[CH2:12][CH2:11][C@@:10]2([CH3:31])[C@@H:15]([CH2:16][CH2:17][C@@H:18]3[C@@H:9]2[C@H:8]([NH:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:25][C@@:23]2([CH3:24])[C@H:19]3[CH2:20][CH2:21][C@@H:22]2[C:26]([O:28][CH3:29])=[O:27])[CH2:14]1)(=[O:45])[CH3:44]

Participants

8

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 12804606HCID 12804606, compound

Product 1

HCID 70477498HCID 70477498, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Methyl 11α-cyclohexylamino-3α-hydroxy-5α-androstane-17β-carboxylate (550 mg) in chloroform (5.5 ml) containing dry PTSA (440 mg) was stirred for 20 min then treated with acetic anhydride (1.0 ml) and left for 18 h. The reaction mixture was diluted with ethanol and evaporated to give an oil. The residue is ethanol (10 ml) was diluted with 5% NaHCO3 solution (50 ml) and water (100 ml) and extracted with ether (3×). The extracts were washed with water (1×), dried and evaporated to give an oil. This was crystallised from methanol to give the title compound (249 mg), m.p. 126°-128°, [α]D +12°.

Workup

  1. waitleft for 18 h
  2. customevaporated
  3. customto give an oil
  4. extractionextracted with ether (3×)
  5. washThe extracts were washed with water (1×)
  6. customdried
  7. customevaporated
  8. customto give an oil
  9. customThis was crystallised from methanol

Sources & evidence

ORD record
ord-84bd8e380f1741f18f1aaaa318cb3a1d
Source dataset
uspto-grants-1985_05
Patent number
US04515786

Reaction notes

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