Dichloromethane → HCID 131725776, compound

HRID 1827304Notes

Reaction equation

HRID 1827304 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClCCl.[CH2:20]([C@@:27]1([OH:50])[C@@:31]2([CH2:41][O:42][C@H:28]1[C@H:29]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[OH:49])[O:30]2)[CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[C:1]([O:49][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=1[C@@H:29]1[O:30][C@:31]2([CH2:32][O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@@:27]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([OH:50])[C@H:28]1[O:42][CH2:41]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 131725774HCID 131725774, compound

Product 1

HCID 131725776HCID 131725776, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzoyl chloride (0.06 ml, 0.52 mmol) and anhydrous triethylamine (0.073 ml, 0.52 mmol) were added to an anhydrous dichloromethane (3 ml) solution of the compound (24) (168 mg, 0.40 mmol), and the mixture was stirred for 3 hours at room temperature. After water was added to the reaction solution, the system was extracted with ethyl acetate 3 times. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:1) to obtain a colorless oily substance (25) (209 mg, 93%).

Workup

  1. extractionthe system was extracted with ethyl acetate 3 times
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-7003d344d2fd47eead8f8eeec634588d
Source dataset
uspto-grants-2006_05
Patent number
US07053199B2

Reaction notes

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