Methyl triflate → HCID 86645807, compound

HRID 1695171Notes

Reaction equation

HRID 1695171 reaction equation
[C:1]([O:5][C:6](=[O:21])[C@H:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C@H:8]([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].[C:22](C1C=CC=C(C(C)(C)C)N=1)(C)(C)C.O(C)S(C(F)(F)F)(=O)=O.[Cl-].[NH4+]>ClCCl>[C:1]([O:5][C:6](=[O:21])[C@H:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C@H:8]([O:15][CH3:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 9526Methyl triflateHCID 25517Ammonium ChlorideHCID 685102,6-Di-tert-butylpyridineHCID 86645803HCID 86645803, compound

Product 1

HCID 86645807HCID 86645807, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The (2R,3R)-3-hydroxy-2-pentylnonanoic acid t-butyl ester (500 mg, 1.66 mmol) obtained in Production Example C-3 was dissolved in anhydrous dichloromethane (5.0 ml). Then, 2,6-di-t-butylpyridine (476 mg, 2.49 mmol) was added thereto to be stirred for 5 minutes at room temperature. Methyl triflate (328 mg, 1.99 mmol) was added to the obtained mixture, which was heated to 40° C. and stirred for 20 hours. An aqueous saturated ammonium chloride solution was added to the reaction solution, which was extracted 3 times with dichloromethane. The resulting organic layer was dried with anhydrous magnesium sulfate, filtered, and condensed. The obtained residue was purified by column chromatography (silica gel: 25 g, n-hexane/ethyl acetate=20/1) to produce the target compound (498 mg, 95%).

Workup

  1. temperaturewas heated to 40° C.
  2. stirringstirred for 20 hours
  3. extractionwas extracted 3 times with dichloromethane
  4. dry with materialThe resulting organic layer was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customcondensed
  7. customThe obtained residue was purified by column chromatography (silica gel: 25 g, n-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-cb8d5ebeae244b91b6ac4a039057da98
Source dataset
uspto-grants-2012_04
Patent number
US08163713B2

Reaction notes

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