Hydrochloric Acid → HCID 66937909, compound

HRID 1160572Notes

Reaction equation

HRID 1160572 reaction equation
[Si:1]([O:8][C@H:9]([CH2:14][CH2:15][C@:16]1([CH3:29])[C@H:20]([CH:21]=[CH2:22])[O:19][C@H:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:17]1)[CH2:10][C:11]([OH:13])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.[CH3:49][O:50][C:51]1[CH:68]=[CH:67][C:54]([CH2:55][O:56][CH2:57]/[CH:58]=[C:59](\[CH3:66])/[C@@H:60](O)[C@@H:61]([CH3:64])[CH:62]=[CH2:63])=[CH:53][CH:52]=1.Cl>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1.C1COCC1>[Si:1]([O:8][CH:9]([CH2:14][CH2:15][C@:16]1([CH3:29])[C@H:20]([CH:21]=[CH2:22])[O:19][C@H:18]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[O:17]1)[CH2:10][C:11]([O:13][C@@H:60]([C@@H:61]([CH3:64])[CH:62]=[CH2:63])/[C:59](/[CH3:66])=[CH:58]/[CH2:57][O:56][CH2:55][C:54]1[CH:67]=[CH:68][C:51]([O:50][CH3:49])=[CH:52][CH:53]=1)=[O:12])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 16732377HCID 16732377, compoundHCID 16732378HCID 16732378, compound

Product 1

HCID 66937909HCID 66937909, compoundYield 93.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To an anhydrous THF (130 ml) solution of (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(2S,4R,5S)-4-methyl-2-phenyl-5-vinyl-1,3-dioxolan-4-yl] pentanoic acid (6.50 g, 15.5 mmol) was added triethylamine (2.80 ml, 20.2 mmol) under nitrogen atmosphere and cooled to 0° C. 2,4,6-Trichlorobenzoyl chloride (2.65 ml, 17.0 mmol) was added to the reaction solution. After the reaction solution was stirred at 0° C. for 10 minutes, it was stirred at room temperature for two hours. After the reaction solution was filtered with celite, the organic layer was concentrated under reduced pressure. To the obtained residue, an anhydrous toluene (130 ml) solution of (3S,4S,5E)-7-[(4-methoxybenzyl)oxy]-3,5-dimethylhepta-1,5-dien-4-ol (4.71 g, 17.0 mmol) and 4-dimethylaminopyridine (2.46 g, 20.2 mmol) were added under nitrogen atmosphere. After the reaction solution was stirred at room temperature for two hours, it was poured into 0.5N hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution, water and brine sequentially, it was dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=10:1→5:1) to obtain the title compound (9.81 g) as a colorless oil.

Workup

  1. stirringit was stirred at room temperature for two hours
  2. filtrationAfter the reaction solution was filtered with celite
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. stirringAfter the reaction solution was stirred at room temperature for two hours
  5. extractionextracted with ethyl acetate
  6. washAfter the organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution, water and brine sequentially
  7. dry with materialit was dried over anhydrous magnesium sulfate
  8. filtrationAfter the drying agent was filtered off
  9. concentrationthe organic layer was concentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=10:1→5:1)

Sources & evidence

ORD record
ord-3c7afe01aed346cfb32283d3bec14311
Source dataset
uspto-grants-2010_10
Patent number
US07816401B2

Reaction notes

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