HCID 69093719, compound → HCID 69094256, compound

HRID 1396296Notes

Reaction equation

HRID 1396296 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH:18]([OH:20])[CH3:19])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:21]([CH2:29][CH:30]=[CH2:31])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[S:14]2)[C@H:10]1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl>[C:18]([C@H:17]1[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:21]([CH2:29][CH:30]=[CH2:31])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:25])[CH3:26])[S:14]2)[C@@H:10]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:9]1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:20])[CH3:19]

Participants

3

Reactant 1

HCID 69093719HCID 69093719, compound

Product 1

HCID 69094256HCID 69094256, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 143 (6 g, 11 mmol) in dichloromethane (120 mL) was added DMP (6.9 g, 16 mmol). The resulting solution was stirred for 1.5 hours at room temperature, then quenched by saturated aqueous sodium bicarbonate solution (80 mL), and extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (2×50 mL), dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was purified by flash column chromatography with 5%-10% ethyl acetate in petroleum ether to afford 144 as a yellow syrup (4 g, 67%). (ES, m/z): [M+H]+ 553.0; 1H NMR (300 MHz, CDCl3): 7.34-7.19 (m, 10H), 6.10 (d, J=6.9 Hz, 1H), 5.85-5.76 (m, 1H), 5.10-4.94 (m, 2H), 4.69-4.25 (m, 7H), 4.15-4.10 (m, 1H), 3.97-3.83 (m, 2H), 2.19 (s, 3H), 1.50 (s, 9H).

Workup

  1. customquenched by saturated aqueous sodium bicarbonate solution (80 mL)
  2. extractionextracted with dichloromethane (3×100 mL)
  3. washThe combined organic layer was washed with brine (2×50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash column chromatography with 5%-10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-d0fea3e2cc0b435fa94187863ba3bb2a
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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