HCID 70566973, compound → HCID 70567932, compound

HRID 237070Notes

Reaction equation

HRID 237070 reaction equation
[CH3:1][NH:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][C@@H:13]1[C@@H:17](/[CH:18]=[CH:19]/[C@@H:20]([O:26]C2CCCCO2)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:16]([O:33]C2CCCCO2)[CH2:15][C@@H:14]1[O:40][Si](CC1C=CC=CC=1)(CC1C=CC=CC=1)CC1C=CC=CC=1)=[O:4]>C(O)(=O)C.O.O1CCCC1>[CH3:1][NH:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][C@@H:13]1[C@@H:17](/[CH:18]=[CH:19]/[C@@H:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:16]([OH:33])[CH2:15][C@@H:14]1[OH:40])=[O:4]

Participants

3

Reactant 1

HCID 70566973HCID 70566973, compound

Product 1

HCID 70567932HCID 70567932, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

At 50°, 250 mg. of (5Z,13E)-(8R,9S,11R,12R,15S)-1-(N-methylcarbamoyloxy)-11,15-bis(tetrahydropyran-2-yloxy)-9-tribenzylsilyloxy-5,13-prostadiene was stirred for 5 hours in 15 ml. of a mixture of glacial acetic acid/water/tetrahydrofuran (65/35/10). The mixture was evaporated under vacuum and the residue purified by chromatography on silica gel with ether/dioxane (7+3), thus obtaining 105 mg. of the title compound as a colorless oil.

Workup

  1. customAt 50°
  2. customThe mixture was evaporated under vacuum
  3. customthe residue purified by chromatography on silica gel with ether/dioxane (7+3)
  4. customthus obtaining 105 mg

Sources & evidence

ORD record
ord-82f4590be7f14864857b58608f649da4
Source dataset
uspto-grants-1979_06
Patent number
US04159343

Reaction notes

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