Water → HCID 67157815, compound

HRID 901784Notes

Reaction equation

HRID 901784 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:16]([CH2:17][OH:18])[C@@H:15]2[C@H:19]([OH:20])[C@H:12]1[C@H:13]([O:21][CH3:22])[O:14]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].[C:31](Cl)(=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[C@H:16]([CH2:17][O:18][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C@@H:15]2[C@H:19]([O:20][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@H:12]1[C@@H:13]([O:21][CH3:22])[O:14]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 67158248HCID 67158248, compound

Product 1

HCID 67157815HCID 67157815, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

The compound (152 mg, 0.49 mmol) synthesized in Example 7 (7b) was dissolved in pyridine (4 mL) and t-butyldimethylsilyl chloride (82 mg, 0.54 mmol) was added thereto, followed by stirring of the mixture at 0° C. for 3 hours. After it was confirmed by TLC that the raw material was no longer present, benzoyl chloride (86 μL, 0.74 mmol) was added and the mixture was stirred at 0° C. for 1 hour. After water (20 mL) was added thereto at 0° C. and the mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine (20 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 10:1, V/V) to obtain the desired title compound (218 mg, yield 84%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 hour
  2. extractionat 0° C. and the mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine (20 mL)
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationby distilling off of the solvent under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-66a165688c5e4c35b8119a53fcdca7db
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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