Water → HCID 22790350, compound

HRID 1077016Notes

Reaction equation

HRID 1077016 reaction equation
Br[CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@H:13]([OH:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[NH:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]1=[S:32].[OH-].[Na+].O>O1CCCC1.CCOCC>[OH:24][C@@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[C:19](=[O:23])[CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:25])[CH2:2][S:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=2)[CH2:12]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 27236982-MercaptopyridineHCID 8673346721-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Product 1

HCID 22790350HCID 22790350, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 21-bromo-3α-hydroxy-5α-pregnane-11,20-dione (1.0 g.) in tetrahydrofuran (10 ml) was added to a solution of pyrid-2-thione (0.5 g) in 2N-aqueous sodium hydroxide (10 ml). After allowing the mixture to stand at room temperature for 3 mins., water and ether were added. The organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was subjected to preparative t.l.c. and recrystallisation from methyl acetate/petrol to give title compound (240 mg.) as white needles m.p. 184° [α]D + 130° (c 0.9).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customand recrystallisation from methyl acetate/petrol

Sources & evidence

ORD record
ord-506043b8c987439d841b90f07acda679
Source dataset
uspto-grants-1976_05
Patent number
US03959260

Reaction notes

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