Imidazole → Ethyl 2-amino-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-thiazole-5-carboxylate

HRID 1948354Notes

Reaction equation

HRID 1948354 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH2:7][OH:8])[N:6]=1.N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C=O)C>[NH2:1][C:2]1[S:3][C:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH2:7][O:8][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[N:6]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12308573Ethyl 2-amino-4-(hydroxymethyl)thiazole-5-carboxylate2×

Product 1

HCID 59406866Ethyl 2-amino-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-thiazole-5-carboxylateYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.0 g (9.8 mmol) of ethyl 2-amino-4-(hydroxymethyl) -1,3-thiazole-5-carboxylate (Intermediate 209) and 1.3 g (19.4 mmol) of imidazole in 20 ml DMF was added 1.6 g (10.6 mmol) of t-butyldimethylsilyl chloride. After stirring for 2 h, solvent was removed and the residue was taken up in water. Insoluble solids were collected, ground up, washed with water and dried in vacuo to afford 2.95 g of product. MS (ES) (MH+): 317 for C13H24N2O3SSi; NMR (d6-DMSO): 0.03 (s, 6H), 0.86 (s, 9H), 1.2 (t, 3H), 4.1 (q, 2H), 4.8 (s, 2H), 7.8 (s, 2H).

Workup

  1. customsolvent was removed
  2. customInsoluble solids were collected
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4eded98e31c147f991ffaeff006c8086
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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