Nitrogen → HCID 66819916, compound

HRID 42771Notes

Reaction equation

HRID 42771 reaction equation
N#N.C([SiH2][O:8][C:9](C)(C)[C:10]1[S:11][CH:12]=[C:13]([C:15]2([CH3:20])[O:19][CH2:18][CH2:17][O:16]2)[N:14]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CC(=O)OCC>[CH3:20][C:15]1([C:13]2[N:14]=[C:10]([CH2:9][OH:8])[S:11][CH:12]=2)[O:19][CH2:18][CH2:17][O:16]1

Participants

6

Reactant 3

HCID 947NitrogenHCID 2724141Tetrabutylammonium FluorideHCID 1317300012-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

Product 1

HCID 66819916HCID 66819916, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(2-methyl-[1,3]dioxolan-2-yl)-thiazole (1.30 g, 4.12 mmol) in dry THF (10 mL) was treated at 0° C. with TBAF (6.2 mL of a 1M solution in THF, 6.20 mmol). The reaction mixture was stirred at 0° C. for 5 min and at rt for 1 h 30. The mixture was then diluted with EA (10 mL), washed with brine (3×10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (5:1->1:3 hept-EA) gave the title compound as a yellow oil. TLC:rf (1:2 hept-EA)=0.20. LC-MS-conditions 02: tR=0.59 min; [M+H]+=202.48.

Workup

  1. washwashed with brine (3×10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by FC (5:1->1:3 hept-EA)

Sources & evidence

ORD record
ord-ebf29e9a49354656af4226e3f7db034a
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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