Hydrochloric Acid → HCID 131710576, compound

HRID 1973716Notes

Reaction equation

HRID 1973716 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](OCC)=O.[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][C@@H:19]1[CH2:38][CH2:37][C@@:36]2([CH3:39])[C@@H:21]([CH2:22][CH2:23][C@@H:24]3[C@@H:35]2[C:34](=[O:40])[CH2:33][C@@:32]2([CH3:41])[C@H:25]3[CH2:26][CH2:27][C@@H:28]2[C:29](=[O:31])[CH3:30])[CH2:20]1.[H-].[Na+].Cl>CS(C)=O.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:30][C:29](=[O:31])[C@@H:28]1[C@:32]2([CH3:41])[C@H:25]([C@H:24]3[C@H:35]([C:34](=[O:40])[CH2:33]2)[C@:36]2([CH3:39])[C@H:21]([CH2:20][C@H:19]([O:18][CH:13]4[CH2:14][CH2:15][CH2:16][CH2:17][O:12]4)[CH2:38][CH2:37]2)[CH2:22][CH2:23]3)[CH2:26][CH2:27]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 17307Ethyl 2-pyridinecarboxylateHCID 24758Sodium hydrideHCID 131710577HCID 131710577, compound

Product 1

HCID 131710576HCID 131710576, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

Ethyl picolinate (1.0 ml.) was added to a mixture of 3α-(tetrahydropyran-2ξ-yloxy)-5α-pregnane-11,20-dione (840 mg) and sodium hydride (130 mg.) in dry dimethyl sulphoxide (15 ml.). The mixture was stirred, under N2, for 1/2 hr., then treated with methanol and poured into 2N-hydrochloric acid. The precipitate was collected, washed and dried to give 21-picolinyl-3α-(tetrahydropyran-2ξ-yloxy)-5α-pregnane-11,20-dione (695 mg.).

Workup

  1. customThe precipitate was collected
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-40a74cd08e9e4d5690aebe547a91a674
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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