Triethylamine → HCID 59141826, compound

HRID 1437815Notes

Reaction equation

HRID 1437815 reaction equation
C(N(CC)CC)C.[O:8]([C:22]1[CH:27]=[CH:26][C:25]([C@@H:28]2[C@@H:31]([CH2:32][CH2:33][C@@H:34]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[OH:35])[C:30](=[O:43])[N:29]2[C:44]2[CH:49]=[CH:48][C:47](I)=[CH:46][CH:45]=2)=[CH:24][CH:23]=1)[C@@H:9]1[O:17][C@H:16]([C:18]([O:20][CH3:21])=[O:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]1[OH:11].[CH2:51]([NH:54][S:55]([CH3:58])(=[O:57])=[O:56])[C:52]#[CH:53]>CN(C=O)C.[Cu](I)I>[O:8]([C:22]1[CH:27]=[CH:26][C:25]([C@@H:28]2[C@@H:31]([CH2:32][CH2:33][C@@H:34]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[OH:35])[C:30](=[O:43])[N:29]2[C:44]2[CH:49]=[CH:48][C:47]([C:53]#[C:52][CH2:51][NH:54][S:55]([CH3:58])(=[O:57])=[O:56])=[CH:46][CH:45]=2)=[CH:24][CH:23]=1)[C@@H:9]1[O:17][C@H:16]([C:18]([O:20][CH3:21])=[O:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]1[OH:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 14025440N-(Prop-2-yn-1-yl)methanesulfonamideHCID 59076395HCID 59076395, compound

Product 1

HCID 59141826HCID 59141826, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.07 mL, 0.502 mmol) was added to a stirred solution of 4-[(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-(4-iodophenyl)-4-oxoazetidin-2-yl]phenyl methyl β-D-glucopyranosiduronate (i-7) (0.050 g, 0.071 mmol), N-prop-2-yn-1-ylmethanesulfonamide (i-5) (0.014 g, 0.105 mmol), tetrakistriphenylphosphine palladium(0) (0.012 g, 0.010 mmol) and copper iodide (0.005 g, 0.026 mmol) in DMF (0.5 mL) under a nitrogen atmosphere and the resulting solution aged at room temperature for 18 h. The volatiles were evaporated in vacuo and the crude residue purified by flash chromatography on silica gel (gradient elution; 0-25% methanol/methylene chloride as eluent) to afford the title compound; m/z (ES) 713 (MH+), 505.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customthe crude residue purified by flash chromatography on silica gel (gradient elution; 0-25% methanol/methylene chloride as eluent)

Sources & evidence

ORD record
ord-b2fafd385a7f475091bf87cc293d1572
Source dataset
uspto-grants-2009_11
Patent number
US07622449B2

Reaction notes

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