p-Toluenesulfonic acid → HCID 86738594, compound

HRID 223431Notes

Reaction equation

HRID 223431 reaction equation
C1(C)C=CC(S(O)(=O)=[O:8])=CC=1.[NH2:12][C@@H:13]1[CH2:30][C@@:28]2([CH3:29])[C@@H:24]([CH2:25][CH2:26][C@@H:27]2[C:31]([O:33][CH3:34])=[O:32])[C@H:23]2[C@H:14]1[C@:15]1([CH3:35])[C@@H:20]([CH2:21][CH2:22]2)[CH2:19][CH:18]=[CH:17][CH2:16]1.ClC1C=C(C=CC=1)C(OO)=O>ClCCCl>[NH3:12].[NH2:12][C@@H:13]1[CH2:30][C@@:28]2([CH3:29])[C@@H:24]([CH2:25][CH2:26][C@@H:27]2[C:31]([O:33][CH3:34])=[O:32])[C@H:23]2[C@H:14]1[C@:15]1([CH3:35])[C@@H:20]([CH2:21][CH2:22]2)[CH2:19][C@@H:18]2[O:8][C@@H:17]2[CH2:16]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 70297m-Chloroperbenzoic acidHCID 12804689HCID 12804689, compound

Product 2

HCID 222AmmoniaHCID 86738594HCID 86738594, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Toluene-4-sulphonic acid (570 mg) was added to a solution of methyl 11α-amino-5α-androst-2-ene-17β-carboxylate (1.0 g) in 1,2-dichloroethane (25 ml). After 0.5 h m-chloroperoxybenzoic acid (810 mg) was added and the mixture was left for a further 2 h. The mixture was washed with NaHSO3 solution, 5% NaHCO3 solution and water. The aqueous phases were extracted with dichloromethane and the combined organic phase was dried and evaporated to leave a foam which was purified by preparative t.l.c. in MeOH: 0.88 NH3 (50:1) to give the title compound (369 mg) as a foam [α]D +44°, νmax 1722 cm-1.

Workup

  1. washThe mixture was washed with NaHSO3 solution, 5% NaHCO3 solution and water
  2. extractionThe aqueous phases were extracted with dichloromethane
  3. customthe combined organic phase was dried
  4. customevaporated
  5. customto leave a foam which
  6. customwas purified by preparative t.l.c

Sources & evidence

ORD record
ord-7a9d29520beb4a72857da4445430b7b6
Source dataset
uspto-grants-1982_10
Patent number
US04353898

Reaction notes

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