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 1779226ノート

反応式

HRID 1779226 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-0ed038e37559455c8fe1cf6a718e50a1
出典データセット
uspto-grants-2016_02
特許番号
US09266853B2

反応ノート

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