2-Dimethylaminopyridine → (E)-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-en-1-one

HRID 1779234Notes

Reaction equation

HRID 1779234 reaction equation
[CH:1]([C@H:4]1[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][C:6](=[S:21])[NH:5]1)([CH3:3])[CH3:2].CN(C1C=CC=CN=1)C.Cl.CN(C)CCCN=C=NCC.[C:43]1([CH2:49][CH2:50][CH2:51][CH2:52][C:53]2([CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63]/[CH:64]=[CH:65]/[CH2:66][C:67](O)=[O:68])[O:57][CH2:56][CH2:55][O:54]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.P([O-])(O)(O)=O.[Na+]>ClCCl.C(OCC)(=O)C>[CH:1]([C@H:4]1[C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][C:6](=[S:21])[N:5]1[C:67](=[O:68])[CH2:66]/[CH:65]=[CH:64]/[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][C:53]1([CH2:52][CH2:51][CH2:50][CH2:49][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[O:57][CH2:56][CH2:55][O:54]1)([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23672064Monosodium phosphateHCID 39058337(S)-4-Isopropyl-5,5-diphenyloxazolidine-2-thioneHCID 90060189(E)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-enoic acid

Product 1

HCID 90060381(E)-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-en-1-oneYield 54%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(S)-4-Isopropyl-5,5-diphenyl-oxazolidine-2-thione (412 mg, 1.39 mmol) was suspended in dichloromethane (3.3 mL), and then cooled to 0° C. in an ice bath. Dimethylaminopyridine (16 mg, 0.131 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (315 mg, 1.64 mmol) were added in this order. A solution of a commercially available reagent of (E)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-enoic acid (476 mg, 1.27 mmol) in dichloromethane (3.4 mL) was then added. After stirring at 0° C. for 2 hours, an aqueous solution (50 mL) of 10% sodium dihydrogen phosphate and ethyl acetate (50 mL) were added and the mixture was separated. The organic layer was washed with a saturated aqueous solution (40 mL) of sodium chloride, then dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. The residue was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 445 mg (0.681 mmol, 54% yield) of (E)-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-en-1-one (ESI (LC/MS positive mode) m/z 654 (M+H); Rt 3.07 min.).

Workup

  1. customthe mixture was separated
  2. washThe organic layer was washed with a saturated aqueous solution (40 mL) of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified on Biotage (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ac3c38e6f91e4aa2bfb295a09459d534
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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