Sodium Bicarbonate → HCID 11771286, compound

HRID 393567Notes

Reaction equation

HRID 393567 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 h ours, 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, 9H), 0.83 (t, J=7 Hz, 3H), 1.81-1.88 (m, J=7 Hz, 2H), 1.37 (br s, 1H), 3.00 (d, J=14 Hz, 1H), 3.32 (d, J=14 Hz, 1H), 3.91 (s, 3H), 5.18 (d, J=15 Hz, 1H), 5.42 (d, J=15 Hz, 1H), 7.26 (s, 1H); 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-0b9d5d81d4bd4deba475580acdca468b
Source dataset
uspto-grants-2004_10
Patent number
US06809103B2

Reaction notes

Loading…