Triethylamine → HCID 86600678, compound

HRID 2106420Notes

Reaction equation

HRID 2106420 reaction equation
C(N(CC)CC)C.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10].[CH2:14]([O:21][C@@H:22]1[C@@H:28]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:27]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@@H:26]([CH2:45][O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:25][C@@:23]1([C:54]1[CH:59]=[CH:58][C:57]([CH3:60])=[C:56]([CH2:61][C:62]2[CH:67]=[CH:66][C:65](OS(C(F)(F)F)(=O)=O)=[CH:64][CH:63]=2)[CH:55]=1)[OH:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:14]([O:21][C@@H:22]1[C@@H:28]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C@H:27]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@@H:26]([CH2:45][O:46][CH2:47][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[O:25][C@@:23]1([C:54]1[CH:59]=[CH:58][C:57]([CH3:60])=[C:56]([CH2:61][C:62]2[CH:63]=[CH:64][C:65]([C:13]#[C:12][Si:9]([CH3:11])([CH3:10])[CH3:8])=[CH:66][CH:67]=2)[CH:55]=1)[OH:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 66111Trimethylsilylacetylene2×HCID 516892Sodium BicarbonateHCID 86600677HCID 86600677, compound

Product 1

HCID 86600678HCID 86600678, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Under argon, 27 mg copper iodide, 49 mg bis-(triphenylphosphine)-palladium dichloride, 0.30 ml triethylamine and finally 0.14 ml of trimethylsilylacetylene are added to a solution of 0.60 g 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-3-[4-(trifluoromethylsulphonyloxy)-benzyl]-4-methyl-benzene in 3 ml of dimethylformamide. The flask is tightly sealed and stirred for 4 h at 90° C. Then another 20 mg of bis-(triphenylphosphine)-palladium dichloride and 0.6 ml trimethylsilylacetylene are added, and the solution is stirred for a further 4 h at 90° C. Then aqueous sodium hydrogen carbonate solution is added, the mixture is extracted three times with ethyl acetate, and the combined organic phases are dried over sodium sulphate. After the solvent has been eliminated the residue is chromatographed through silica gel (cyclohexane/ethyl acetate 40:1->10:1).

Workup

  1. customThe flask is tightly sealed
  2. stirringthe solution is stirred for a further 4 h at 90° C
  3. extractionthe mixture is extracted three times with ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulphate
  5. customis chromatographed through silica gel (cyclohexane/ethyl acetate 40:1->10:1)

Sources & evidence

ORD record
ord-b1c949004f524a5b86020a263375ee41
Source dataset
uspto-grants-2009_08
Patent number
US07579449B2

Reaction notes

Loading…