Thionyl Chloride → HCID 86686088, compound

HRID 1520753Notes

Reaction equation

HRID 1520753 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C@H:16]1[C@@H:25]([C:26]([OH:28])=[O:27])[C:24]2[C:19](=[CH:20][C:21]([O:31][CH3:32])=[C:22]([O:29][CH3:30])[CH:23]=2)[C:18](=[O:33])[N:17]1[CH3:34])=[O:8].[C:35](=O)(O)[O-].[Na+]>CO>[CH3:5][O:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C@H:16]1[C@H:25]([C:26]([O:28][CH3:35])=[O:27])[C:24]2[C:19](=[CH:20][C:21]([O:31][CH3:32])=[C:22]([O:29][CH3:30])[CH:23]=2)[C:18](=[O:33])[N:17]1[CH3:34])=[O:8]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 86686089HCID 86686089, compound2×

Product 1

HCID 86686088HCID 86686088, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (10 mL) was added slowly to a suspension of cis 10 (0.75 g, 1.8 mmol) and trans 10 (1.35 g, 3.3 mmol) in methanol (100 mL) at 0° C. The resulting mixture was stirred for 6 h at 0° C. After completion of the reaction (TLC), the reaction mixture was poured slowly into a mixture of ice (200 g) and a saturated solution of sodium bicarbonate (100 mL). The resulting mixture was extracted with chloroform (3×150 mL), and the combined extracts were dried with sodium sulfate, filtered though a thin pad of silica gel, and evaporated to dryness to obtain 11 as amorphous glassy solid (2.1 g, 96%). IR (film) 1733, 1637 cm−1; 1H NMR (500 MHz, CDCl3) δ 7.67 (s, 1 H), 7.52 (d, J=7.7 Hz, 1 H), 7.25 (t, J=7.0 Hz, 1 H), 7.03 (t, J=7.5 Hz, 1 H), 6.83 (d, J=7.8 Hz, 1 H), 6.73 (s, 1 H), 6.54 (s, 1 H), 5.45 (s, 1 H), 3.95 (s, 3 H), 3.89 (s, 1 H), 3.82 (s, 3 H), 3.72 (s, 3 H), 3.63 (s, 1 H), 3.03 (s, 3 H); 13C NMR (126 MHz, CDCl3) δ 172.06, 164.17, 155.49, 152.15, 149.18, 134.39, 132.53, 129.10, 126.67, 126.53, 125.93, 125.14, 121.60, 111.86, 110.17, 59.32, 56.29, 56.20, 53.27, 53.06, 48.66, 34.57; ESIMS m/z (rel intensity) 429 (MH+, 100), 451 (56); ESIHRMS m/z MH+ calcd. for C22H24N2O7, 429,1662; found, 429.1665.

Workup

  1. customat 0° C
  2. customAfter completion of the reaction (TLC)
  3. extractionThe resulting mixture was extracted with chloroform (3×150 mL)
  4. dry with materialthe combined extracts were dried with sodium sulfate
  5. filtrationfiltered though a thin pad of silica gel
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-86f58ff6b38946198b1c5e0186393014
Source dataset
uspto-grants-2015_07
Patent number
US09073920B2

Reaction notes

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