Trityl chloride → HCID 67351808, compound

HRID 1670046Notes

Reaction equation

HRID 1670046 reaction equation
[CH2:1]([O:8][C@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@@H:10]1[O:40][CH2:41][CH:42]([CH2:44][OH:45])[OH:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:66](Cl)(=[O:73])[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1>N1C=CC=CC=1.ClCCl>[C:66]([O:43][CH:42]([CH2:41][O:40][C@H:10]1[O:11][C@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:9]1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:44][OH:45])(=[O:73])[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 7412Benzoyl chlorideHCID 67351753HCID 67351753, compound

Product 1

HCID 67351808HCID 67351808, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Glycerol 8 (900 mg, 1.47 mmol) and trityl chloride (490 mg, 1.76 mmol) were dissolved in dry pyridine (60 mL) and heated at 100° C. The disappearance of 8 was monitored by TLC and after 90 min the reaction was cooled to 0° C. and a solution of benzoyl chloride (1.0 g, 7.0 mmol) in dry dichloromethane (10 mL) was added. The reaction was warmed to room temperature and stirring was continued for 2 h. The solvent was removed and the residue was dissolved in chloroform (50 mL), washed with 2M HCl (2×20 mL), saturated sodium bicarbonate solution (2×20 mL), water (25 mL) and dried over magnesium sulfate. The solvent was removed, the residue was dissolved in mixture of dichloromethane and methanol (7:3, 50 mL) and p-TSA (75 mg) was added. The reaction was stirred at room temperature overnight and solvent was removed. The residue was purified over silica [hexane/ether, 8:2 to 7:3 as eluent] to afford the title compound 9 (816 mg, 77%) as a pale syrup; Rf 0.4 (ether/hexane, 2:1); 1H NMR (500 MHz, CDCl3) δ 8.05 br (d, 3H, J 7.5 Hz), 7.51 (t, 2H, J.5 Hz), 7.41-7.12 and 7.18-7.10 (m, 20 Hs, Ar—H), 5.30-5.20 (m, 1H, H-2′), 4.94 and 4.89 (2×d, each 1H, J 2 Hz, H-1), 4.85 and 4.83 (2×d, each 1H, J 10.5 Hz, PhCH2), 4.77-4.46 (m, 7H), 4.05-3.62 (m, 10H); 13C NMR (125 MHz, CDCl3) δ 166.1, 166.0 (CO), 138.3, 138.2, 138.1, 138.05 (ipso-C), 133.0, 132.96, 129.8, 129.7, 129.6, 129.5, 128.3, 128.2, 128.2, 128.13, 128.10, 128.07, 127.83, 127.80, 127.74, 127.65, 127.62, 127.59, 127.56, 127.41, 127.38, 127.36, 127.32 (CH—Ar), 98.0 and 97.5 (C-1), 79.7, 79.6, 74.8, 74.7, 74.6, 73.8, 73.4, 73.2, 73.1, 72.4, 72.0, 71.9, 69.0, 68.9, 65.6, 65.3, 65.25, 61.2, 57.9; νmax/cm−1 (CHCl3) 1716; LRMS-ESI (+ve) m/z 742 [MNa]+ (100); HRMS-ESI (+ve) (Found: m/z 719.3220 (MH+). C44H47O9 requires m/z 719.3220).

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. temperatureThe reaction was warmed to room temperature
  3. waitwas continued for 2 h
  4. customThe solvent was removed
  5. dissolutionthe residue was dissolved in chloroform (50 mL)
  6. washwashed with 2M HCl (2×20 mL), saturated sodium bicarbonate solution (2×20 mL), water (25 mL)
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed
  9. dissolutionthe residue was dissolved in mixture of dichloromethane and methanol (7:3, 50 mL) and p-TSA (75 mg)
  10. additionwas added
  11. stirringThe reaction was stirred at room temperature overnight
  12. customsolvent was removed
  13. customThe residue was purified over silica [hexane/ether, 8:2 to 7:3 as eluent]

Sources & evidence

ORD record
ord-096fee40cd0c40dfb98dbc1ae34a8f27
Source dataset
uspto-grants-2011_08
Patent number
US07989602B2

Reaction notes

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