Sulfuric Acid → HCID 70479289, compound

HRID 615185Notes

Reaction equation

HRID 615185 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][C@H:16]1[NH:21][C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23])([CH3:14])[C@@H:12]([C:30]([O:32][CH3:33])=[O:31])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.S(=O)(=O)(O)[OH:35]>O1CCOCC1.O>[OH:1][C@H:2]1[CH2:19][C@@:18]2([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[C@H:16]([NH:21][C:22]([O:24][CH2:25][C:26]([Cl:28])([Cl:29])[Cl:27])=[O:23])[CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:30]([O:32][CH3:33])=[O:31])[CH2:4][C@@H:3]1[OH:35]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 86739909HCID 86739909, compound

Product 1

HCID 70479289HCID 70479289, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 2α,3α-epoxy-11α-(2,2,2-trichloroethoxycarbonylamino)-5α-androstane-17β-carboxylate (522 mg) in dioxan (5 ml) was treated with 2N sulphuric acid (1 ml) and stirred at ambient temperature for 18 h. The mixture was diluted with water (50 ml) and extracted with ethyl acetate (3×). The extract was washed with water, dried and evaporated to give a foam. This was purified by preparative t.l.c. in ethyl acetate/petrol (1:1) and crystallised from ether to give the title compound (217 mg) m.p. 228°-230°, [α]D +27.6.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe extract was washed with water
  3. customdried
  4. customevaporated
  5. customto give a foam
  6. customThis was purified by preparative t.l.c
  7. customin ethyl acetate/petrol (1:1) and crystallised from ether

Sources & evidence

ORD record
ord-4f07258d61da4de2bdbc1271899094c5
Source dataset
uspto-grants-1985_02
Patent number
US04497805

Reaction notes

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