Methanesulfonyl chloride → HCID 87687495, compound

HRID 1396271Notes

Reaction equation

HRID 1396271 reaction equation
[CH2:1]([O:8][C@@H:9]([C@@H:12]1[O:20][C@H:19]2[C@H:15]([N:16]=[C:17]([N:21]([CH3:23])[CH3:22])[S:18]2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>ClCCl>[CH3:40][S:41]([O:11][CH2:10][C@H:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:12]1[O:20][C@H:19]2[C@H:15]([N:16]=[C:17]([N:21]([CH3:23])[CH3:22])[S:18]2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:13]1[O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)(=[O:43])=[O:42]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 117716498HCID 117716498, compound

Product 1

HCID 87687495HCID 87687495, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 102 (1.2 g, 2.2 mmol) (Prepared according to the synthesis of Examples 151 and 152, step 1) in dichloromethane (30 mL) was added TEA (664 mg, 6.6 mmol) and MsCl (499 mg, 4.4 mmol) at 0° C. After kept 2 hours at room temperature, the reaction was quenched by water (100 mL) and extracted with dichloromethane (3×30 mL). The combined organic layer was washed with brine (20 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrates were concentrated to give a residue, which was purified by silica gel column with 10%-30% ethyl acetate in petroleum ether to give the title compound (1.1 g, 80%) as brown syrup; (ES, m/z): [M+H]+ 627.0; 1H NMR (300 MHz, CDCl3) δ 7.22-7.45 (m, 15H), 6.35 (d, J=6.3 Hz, 1H), 5.03-5.15 (m, 2H), 4.61-4.80 (m, 4H), 4.47-4.53 (m, 2H), 4.25-4.36 (m, 1H), 4.08-4.12 (m, 1H), 3.89-3.92 (m, 1H), 3.46-3.78 (m, 2H), 3.06 (s, 6H), 3.01 (s, 3H).

Workup

  1. customthe reaction was quenched by water (100 mL)
  2. extractionextracted with dichloromethane (3×30 mL)
  3. washThe combined organic layer was washed with brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrates were concentrated
  7. customto give a residue, which
  8. customwas purified by silica gel column with 10%-30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-34a0bd8cf487416e8c874b6f0bf31a7e
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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