Benzoyl chloride → HCID 66693523, compound

HRID 1469193Notes

Reaction equation

HRID 1469193 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH:9]2[C@H:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:12]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@@H:11]([CH2:39][O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[O:10]2)=[CH:5][C:6]=1[CH2:7][OH:8].CCN(CC)CC.[C:55](Cl)(=[O:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>C(Cl)Cl>[C:55]([O:8][CH2:7][C:6]1[CH:5]=[C:4]([C@H:9]2[C@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:12]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C@@H:11]([CH2:39][O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[O:10]2)[S:3][C:2]=1[Cl:1])(=[O:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 66693020HCID 66693020, compound

Product 1

HCID 66693523HCID 66693523, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of alcohol 35 (5.2 g, 7.75 mmol) in CH2Cl2 (50 mL) were added Et3N (3.5 mL, 23.3 mmol) and benzoyl chloride (1.2 mL, 10.1 mmol) at 0° C. The mixture was allowed to slowly warm to room temperature and stirred at room temperature for 15 hours. The mixture was washed with aq. saturated NaHCO3 solution. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the mixture of anomers of the title compound (6.1 g). The anomeric mixture of 36 was recrystallized with EtOH (50 mL). The precipitate was collected by filtration and washed with cold EtOH (30 mL) and dried under high vacuum to obtain β-anomer of the title compound 36 (4.64 g, 77%).

Workup

  1. washThe mixture was washed with aq. saturated NaHCO3 solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica column chromatography (Biotage)
  6. customto provide

Sources & evidence

ORD record
ord-e22d231b8dea4691b5882a47cc496b64
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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