Triphenylphosphine → 3beta-Acetylthio-14beta,15beta-epoxy-17beta-(3-furyl)-5beta-androstane

HRID 233656Notes

Reaction equation

HRID 233656 reaction equation
N(C(OC(C)C)=O)=NC([O:5][CH:6]([CH3:8])C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:34]1[C@@H:36]2[CH2:37][C@H:38]([C:55]3[CH:59]=[CH:58][O:57][CH:56]=3)[C@:39]3([CH2:41][CH2:42][C@H:43]4[C@H:52]([C@@:35]123)[CH2:51][CH2:50][C@H:49]1[C@:44]4([CH3:54])[CH2:45][CH2:46][C@@H:47](O)[CH2:48]1)[CH3:40].[S:60]1C=CC=C1CC(O)=O>O1CCCC1>[C:6]([S:60][C@H:47]1[CH2:46][CH2:45][C@@:44]2([CH3:54])[C@H:49]([CH2:50][CH2:51][C@@H:52]3[C@@H:43]2[CH2:42][CH2:41][C@@:39]2([CH3:40])[C@:35]43[O:34][C@@H:36]4[CH2:37][C@@H:38]2[C:55]2[CH:59]=[CH:58][O:57][CH:56]=2)[CH2:48]1)(=[O:5])[CH3:8]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 8674878914beta,15beta-Epoxy-17beta-(3-furyl)-5beta-androstan-3alpha-ol

Product 1

HCID 867487913beta-Acetylthio-14beta,15beta-epoxy-17beta-(3-furyl)-5beta-androstane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropyl azodicarboxylate (3.5 ml) was added to a solution of 4.5 g of triphenylphosphine in 85 ml of tetrahydrofuran at 0° C. and the mixture was stirred for 30'. To this mixture a solution of 2.0 g of 14β,15β-epoxy-17β-(3-furyl)-5β-androstan-3α-ol and 2.05 ml of thiolacetic acid in 90 ml of tetrahydrofuran was added dropwise and the resulting mixture was stirred for an hr at room temperature. The solvent was evaporated to dryness under reduced pressure and the crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 95/5 as eluant to give 1.7 g of the title compound (VI-b) as a white solid.

Workup

  1. stirringthe resulting mixture was stirred for an hr at room temperature
  2. customThe solvent was evaporated to dryness under reduced pressure
  3. customthe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-2aa7db8ec55f4722b19975ccdb37f3a8
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Reaction notes

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