Urea → Acetate

HRID 918401Notes

Reaction equation

HRID 918401 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH:9]=[N+]=[N-].NC(N)=O.CCOCC.[OH:21][C@H:22]1[CH2:42][C@@:41]2([CH3:43])[C@@H:33]([CH2:34][C@@H:35]([OH:45])[C@:36]2([OH:44])[C:37](=[O:40])[CH2:38][OH:39])[C@H:32]2[C@H:23]1[C@:24]1([CH3:47])[C:29]([CH2:30][CH2:31]2)=[CH:28][C:27](=[O:46])[CH:26]=[CH:25]1>CO>[C:2]([O-:7])(=[O:1])[CH3:3].[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][O:45][C@@H:35]1[CH2:34][C@@H:33]2[C@:41]([CH3:43])([CH2:42][C@H:22]([OH:21])[C@H:23]3[C@H:32]2[CH2:31][CH2:30][C:29]2[C@:24]3([CH3:47])[CH:25]=[CH:26][C:27](=[O:46])[CH:28]=2)[C@@:36]1([OH:44])[C:37](=[O:40])[CH2:38][OH:39]

Participants

7

Reactant 4

HCID 1176UreaHCID 3283Diethyl EtherHCID 1104705616alpha-HydroxyprednisoloneHCID 215208792-(2-Diazoethoxy)oxane

Product 2

HCID 175AcetateHCID 2279177516alpha-[2-(Tetrahydropyran-2-yloxy)ethoxy]-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(tetrahydropyran-2-yloxy)-1-diazoethane (prepared from 69.1 g of N-]2-(tetrahydropyran-2-yloxy)ethyl]urea by the procedure described in (a) - (e) above) in 600 ml of 3:1 ether-pentane is stirred with 200 ml each of ether and methanol at 0°C. Fourteen g of 11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, 16,17-cycloborate is added in portions. After nitrogen evolution ceases the solvents are removed in vacuo and the residue is dissolved in chloroform and chromatographed on a 150 g-silica gel column. Elution with chloroform and then 1:1 chloroformethyl acetate gives 4.0 g of TLC pure 16α-[2-(tetrahydropyran-2-yloxy)ethoxy]-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione.

Workup

  1. customare removed in vacuo
  2. dissolutionthe residue is dissolved in chloroform
  3. customchromatographed on a 150 g-silica gel column
  4. washElution with chloroform

Sources & evidence

ORD record
ord-a3fbdd4fd094404588f7ef51363ee9c3
Source dataset
uspto-grants-1976_07
Patent number
US03971773

Reaction notes

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