Triethylamine → HCID 25131204, compound

HRID 2076945Notes

Reaction equation

HRID 2076945 reaction equation
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[CH2:13]([C@@H:20]1[CH2:24][O:23][C:22](=[O:25])[N:21]1[C:26]([C@@H:28]1[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][C@H:29]1[CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:27])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C[Si](C)(C)[O:46][CH2:47][CH2:48]O[Si](C)(C)C.C(N(CC)CC)C>C(Cl)Cl>[CH2:13]([C@@H:20]1[CH2:24][O:23][C:22](=[O:25])[N:21]1[C:26]([C@@H:28]1[CH2:33][CH2:32][C:31]2([O:46][CH2:47][CH2:48][O:34]2)[CH2:30][C@H:29]1[CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:27])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 818582,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctaneHCID 25130203HCID 25130203, compound

Product 1

HCID 25131204HCID 25131204, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyl trifluoromethanesulfonate (2.5 mL) was added dropwise to a 0° C. solution of (4R)-4-benzyl-3-({(1R,2R)-2-[(benzyloxy)methyl]-4-oxocyclohexyl}carbonyl)-1,3-oxazolidin-2-one (57.89 g, 138 mmol) and 1,2-bis-(trimethylsilyloxy)ethane (35.4 g, 172 mmol) in CH2Cl2 (400 mL) followed by stirring at rt for 4 h. Triethylamine (3 mL) was then added at 0° C. and the mixture was washed with saturated aqueous NaHCO3 solution and dried over Na2SO4. Concentration in vacuo gave (4R)-4-benzyl-3-({(7R,8R)-7-[(benzyloxy)methyl]-1,4-dioxaspiro[4.5]dec-8-yl}carbonyl)-1,3-oxazolidin-2-one as a thick, tan colored syrup. 1H NMR (500 MHz, d6-acetone) δ 7.36-7.22 (10H, m), 4.48 (1H, m), 4.42 (2H, s), 4.11 (1H, dd, J= 3.1, 8.9 Hz), 3.97 (4H, m), 3.94-3.90 (1H, t, J= 9.0 Hz), 3.67 (1H, m), 3.44-3.38 (2H, m), 3.09 (1H, dd, J= 3.3, 13.5 Hz), 2.92 (1H, dd, J= 8.3, 13.5 Hz), 2.52 (1H, m), 1.97 (1H, m), 1.86-1.76 (3H, m), 1.57-1.50 (1H, m), 1.44 (1H, t, J= 12.8 Hz).

Workup

  1. washthe mixture was washed with saturated aqueous NaHCO3 solution
  2. dry with materialdried over Na2SO4
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-c3853562298e4e4ba3d40dcac7b2f274
Source dataset
uspto-grants-2011_04
Patent number
US07928091B2

Reaction notes

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