Acetic Anhydride → HCID 67058110, compound

HRID 1515098Notes

Reaction equation

HRID 1515098 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[N:22]=[CH:21][C:20]([CH:23]([OH:46])[CH2:24][CH2:25][O:26][C:27]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:19][CH:18]=2)[CH:10]=1.[C:47](OC(=O)C)(=[O:49])[CH3:48].[Cl-].C(=O)(O)O.[Na+]>N1C=CC=CC=1>[C:47]([O:46][CH:23]([C:20]1[CH:21]=[N:22][C:17]([O:16][CH2:15][C:11]2[CH:10]=[C:9]([C:3]3[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[CH:14]=[CH:13][CH:12]=2)=[CH:18][CH:19]=1)[CH2:24][CH2:25][O:26][C:27]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)(=[O:49])[CH3:48]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 23687706HCID 23687706, compoundHCID 67058149HCID 67058149, compound

Product 1

HCID 67058110HCID 67058110, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

1-{6-[(2′,6′-Dimethylbiphenyl-3-yl)methoxy]pyridin-3-yl}-3-(trityloxy)propan-1-ol (250 mg, 0.413 mmol) produced in Example 31 (31C) was dissolved in pyridine (3.0 mL), and acetic anhydride (0.116 mL, 1.24 mmol) was added thereto at 0° C., and then, the resulting mixture was stirred under a nitrogen atmosphere at 65° C. for 4 hours. To the reaction solution, a saturated sodium bicarbonate chloride solution was added, and the organic matter was extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution and a saturated sodium chloride solution, then dried over anhydrous sodium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 80:20 (v/v)), whereby the objective title compound was obtained (212 mg, yield: 79%).

Workup

  1. extractionthe organic matter was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium bicarbonate solution
  3. dry with materiala saturated sodium chloride solution, then dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  6. customwas obtained
  7. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 80:20 (v/v)), whereby the objective title compound
  8. customwas obtained (212 mg, yield: 79%)

Sources & evidence

ORD record
ord-5ed920490b59497faa14600abeb8adc6
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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