Benzoyl chloride → HCID 131733343, compound

HRID 517378Notes

Reaction equation

HRID 517378 reaction equation
O[C@@H:2]1[C@H:6]([CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C@@H:5](/[CH:16]=[CH:17]/[C@@H:18]([O:31][Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[C@H:4]([O:39][Si:40]([CH2:45][CH3:46])([CH2:43][CH3:44])[CH2:41][CH3:42])[CH2:3]1.C(Cl)(=O)C1C=CC=CC=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:45]([Si:40]([CH2:41][CH3:42])([CH2:43][CH3:44])[O:39][C@@H:4]1[CH2:3][C@@H:2]2[O:14][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][C@@H:6]2[C@H:5]1/[CH:16]=[CH:17]/[C@@H:18]([O:31][Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)[CH3:46]

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 131733341HCID 131733341, compound2×

Product 1

HCID 131733343HCID 131733343, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (Z)-7-((1R,2R,3R,5S)-5-hydroxy-3-((triethylsilyl)oxy)-2-((R,E)-3-((triethylsilyl)oxy)-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoic acid (1.5 g, 2.19 mmole) and N,N-diisopropylethylamine (0.48 g from Example 16) in methylene chloride (30 mL) at room temperature under nitrogen, benzoyl chloride (0.30 g, 2.13 mmole) was added and the resulting mixture was stirred for 1 hr at room temperature. The reaction mixture was cooled to −15 to −20° C. and a solution of 4-dimethylaminopyridine (0.45 g, 3.69 mmole) in methylene chloride (5 mL) was added dropwise over 5 minutes. The reaction mixture was further stirred for 30 minutes at −15 to −16° C. The reaction mixture was quenched with saturated sodium bicarbonate solution (30 mL). The organic layer was separated. The aqueous layer was extracted with methylene chloride (30 mL). The combined organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 2.7 g of crude title compound. The crude title compound was purified by column chromatography providing 0.9 g of the title compound. (61.6% yield).

Workup

  1. temperatureThe reaction mixture was cooled to −15 to −20° C.
  2. stirringThe reaction mixture was further stirred for 30 minutes at −15 to −16° C
  3. customThe reaction mixture was quenched with saturated sodium bicarbonate solution (30 mL)
  4. customThe organic layer was separated
  5. extractionThe aqueous layer was extracted with methylene chloride (30 mL)
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give 2.7 g of crude title compound
  10. customThe crude title compound was purified by column chromatography

Sources & evidence

ORD record
ord-9b8b35e689a347d9986d0dd44a345db2
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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