Acetic Anhydride → 3-(tert-Butoxycarbonylamino)-1-(2-phenyl-1,3-dithiaN-2-yl)cyclohexyl acetate

HRID 530856ノート

反応式

HRID 530856 の反応式
[C:1]1([CH:7]2[S:12][CH2:11][CH2:10][CH2:9][S:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].C1C[O:24][CH2:23][CH2:22]1.CCCCCCC.C(C1C=CC=CC=1)C.[O:41]=[C:42]1[CH2:47][CH2:46][CH2:45][CH:44]([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[CH2:43]1.C(OC(=O)C)(=O)C>C1COCC1.O>[C:23]([O:41][C:42]1([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:8][CH2:9][CH2:10][CH2:11][S:12]2)[CH2:47][CH2:46][CH2:45][CH:44]([NH:48][C:49]([O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:55])[CH2:43]1)(=[O:24])[CH3:22]

参加物

8

反応物 5

HCID 7918Acetic AnhydrideHCID 215472-Phenyl-1,3-dithianeHCID 2724682Lithium diisopropylamideHCID 22742125Tetrahydrofuran heptane ethylbenzolHCID 44228975(3-Oxo-cyclohexyl)-carbamic acid tert-butyl ester

生成物 1

HCID 866982403-(tert-Butoxycarbonylamino)-1-(2-phenyl-1,3-dithiaN-2-yl)cyclohexyl acetate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

To a solution of 2-phenyl-1,3-dithiane (12 mmol, 2.35 g) in THF (15 mL) at 78° C. was added a solution of lithium diisopropylamide in THF/heptane/ethylbenzene (12 mmol, 1.8 M, 6.7 mL) under argon. The reaction mixture was warmed up to −20° C. and stirred for 30 minutes at −20° C. The reaction mixture was cooled down to −78° C. tert-Butyl 3-oxocyclohexylcarbamate (5 mmol, 1.065 g) in THF was added. The reaction mixture was allowed to warm up to room temperature and stirred for overnight. Acetic anhydride (20 mmol, 1.9 mL) was added. The reaction mixture was stirred at room temperature for 4 hours. Water was added. The organics were extracted with EtOAc. 3-(tert-Butoxycarbonylamino)-1-(2-phenyl-1,3-dithiaN-2-yl)cyclohexyl acetate was obtained after purification by silica gel column chromatography.

後処理

  1. additionwas added
  2. temperatureto warm up to room temperature
  3. stirringstirred for overnight
  4. stirringThe reaction mixture was stirred at room temperature for 4 hours
  5. extractionThe organics were extracted with EtOAc

出典と根拠

ORDレコード
ord-4a1af14b5b734e9facdf6a7847e6fe81
出典データセット
uspto-grants-2016_05
特許番号
US09351965B2

反応ノート

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