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

HRID 530858노트

반응식

HRID 530858 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ff08b2de137f4f59a526e402c0e04998
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09351965B2

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