Sodium Bicarbonate → HCID 11771286, compound

HRID 495050Notes

Reaction equation

HRID 495050 reaction equation
C([O:5][C:6](=O)[CH2:7][C:8]([OH:25])([C:11]1[CH:16]=[C:15]([Si:17]([CH3:20])([CH3:19])[CH3:18])[N:14]=[C:13]([O:21][CH3:22])[C:12]=1[CH2:23][OH:24])[CH2:9][CH3:10])(C)(C)C.C([O-])(O)=O.[Na+]>FC(F)(F)C(O)=O>[CH2:9]([C:8]1([OH:25])[C:11]2[C:12](=[C:13]([O:21][CH3:22])[N:14]=[C:15]([Si:17]([CH3:18])([CH3:19])[CH3:20])[CH:16]=2)[CH2:23][O:24][C:6](=[O:5])[CH2:7]1)[CH3:10]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 12047796HCID 12047796, compound

Product 1

HCID 11771286HCID 11771286, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a 100 mL flask was added the beta hydroxy ester (6) (0.75 g, 1.9 mmol) followed by trifluoroacetic acid (150 mL). After 24 hours, the mixture was poured into sat. NaHCO3 (pH 8) and extracted with ether (3×100 mL). The organic phase was dried (MgSO4) and chromatographed (hexanes:EtOAc 2:1) to give beta-hydroxy lactone (7) 0.48 g (79%) as a white solid: IR (CHCl3, cm−1) 3020, 2978, 2873, 1742, 1561, 1448, 1384, 1348, 1110, 909, 842; 1H NMR (300 MHz, CDCl3) δ 0.22 (s, 9 H), 0.83 (t, J=7 Hz, 3 H), 1.81-1.88 (m, J=7 Hz, 2 H), 1.37 (br s, 1 H), 3.00 (d, J=14 Hz, 1 H), 3.32 (d, J=14 Hz, 1 H), 3.91 (s, 3 H), 5.18. (d, J=15 Hz, 1 H), 5.42 (d, J=15 Hz, 1 H), 7.26 (s, 1 H); 13C NMR (75 MHz, CDCl3) δ −1.9, 8.4, 33.9, 42.9, 53.8, 62.2, 73.8, 114.7, 121.2, 151.6, 159.8, 165.9, 172.3; HRMS (EI) m/z calcd for C15H23NO4Si (M+) 309.1396, found 309.1399 LRMS (EI) m/z 309 (M+), 294, 266, 252, 238, 89.

Workup

  1. extractionextracted with ether (3×100 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customchromatographed (hexanes:EtOAc 2:1)

Sources & evidence

ORD record
ord-9210dff7527f4d0a88ebbfa8b20bd630
Source dataset
uspto-grants-2009_05
Patent number
US07538220B2

Reaction notes

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