Triethylamine → HCID 53732594, compound

HRID 275086Notes

Reaction equation

HRID 275086 reaction equation
N1C=CN=C1[C:6]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:24]([CH2:25][CH2:26][C@:10]12[CH3:11])[C@@H:23]1[C:18]([CH:19]=[C:20]([O:27][CH2:28][O:29][CH3:30])[CH:21]=[CH:22]1)=[CH:17][CH2:16]3)=[O:7].Cl.[CH3:32][O:33][C:34](=[O:37])[CH2:35][NH2:36].C(N(CC)CC)C.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>O1CCOCC1.O>[CH3:32][O:33][C:34]([CH2:35][NH:36][C:6]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:24]([CH2:25][CH2:26][C@:10]12[CH3:11])[C@@H:23]1[C:18]([CH:19]=[C:20]([O:27][CH2:28][O:29][CH3:30])[CH:21]=[CH:22]1)=[CH:17][CH2:16]3)=[O:7])=[O:37]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 53659642HCID 53659642, compound

Product 1

HCID 53732594HCID 53732594, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 17β-imidazolylcarbonyloxy-3-methoxymethyloxy-1,3,5-estratriene (1.14 g) in dioxane (25 ml) were added glycine methyl ester hydrochloride (1.05 g), triethylamine (1.16 ml), and diazabicycloundecene (1.25 ml). The resultant mixture was refluxed under heating and stirring for 3 days. After cooling, the reaction mixture was mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was chromatographed on a silica gel column (100 g), eluting with hexane-ethyl acetate to give 17β-methoxycarbonylmethylaminocarbonyloxy-3-methoxymethyloxy-1,3,5-estratriene (0.77 g, Yield: 64%).

Workup

  1. temperatureunder heating
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was chromatographed on a silica gel column (100 g)
  8. washeluting with hexane-ethyl acetate

Sources & evidence

ORD record
ord-32f96d7b35af4b5bb075b05d12083de3
Source dataset
uspto-grants-1995_02
Patent number
US05391776

Reaction notes

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