2-Dimethylaminopyridine → 2-trimethylsilanyl-ethyl [(E)-9-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-9-oxo-non-6-enyl]-carbamate

HRID 1779226Notes

Reaction equation

HRID 1779226 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.[CH3:43][Si:44]([CH3:63])([CH3:62])[CH2:45][CH2:46][O:47][C:48]([NH:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]/[CH:56]=[CH:57]/[CH2:58][C:59](O)=[O:60])=[O:49].P([O-])(O)(O)=O.[K+]>ClCCl>[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:59](=[O:60])[CH2:58]/[CH:57]=[CH:56]/[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][NH:50][C:48](=[O:49])[O:47][CH2:46][CH2:45][Si:44]([CH3:43])([CH3:63])[CH3:62])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 218852-DimethylaminopyridineHCID 516951Monobasic potassium phosphateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 39058337(S)-4-Isopropyl-5,5-diphenyloxazolidine-2-thioneHCID 90060233(E)-9-(2-trimethylsilanyl-ethoxycarbonylamino)-non-3-enoic acid

Product 1

HCID 900602442-trimethylsilanyl-ethyl [(E)-9-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-9-oxo-non-6-enyl]-carbamateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

(S)-4-Isopropyl-5,5-diphenyl-oxazolidine-2-thione (2.3 g, 8.28 mmol) was suspended in dichloromethane (17.5 mL), and the mixture was then cooled to 0° C. in an ice bath. Dimethylaminopyridine (97 mg, 0.794 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.00 g, 10.4 mmol) were added and the mixture was then stirred for 25 minutes. To this suspension was added a solution of (E)-9-(2-trimethylsilanyl-ethoxycarbonylamino)-non-3-enoic acid (2.50 g, 7.92 mmol) in dichloromethane (17.5 mL). After stirring at 0° C. for 7.5 hours, an aqueous solution (50 mL) of 10% potassium dihydrogen phosphate and dichloromethane (40 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 3.01 g (5.06 mmol, yield 64%) of 2-trimethylsilanyl-ethyl [(E)-9-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-9-oxo-non-6-enyl]-carbamate.

Workup

  1. stirringAfter stirring at 0° C. for 7.5 hours
  2. customthe mixture was separated
  3. washThe organic layer was washed with a saturated aqueous solution (40 mL) of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified on Biotage (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0ed038e37559455c8fe1cf6a718e50a1
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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