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Hydrochloric Acid → tert-butyl [(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]carbamate

HRID 522379
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HRID 522379 반응식
[C:1]([O:5][C:6]([NH:8][C@:9]1([C:14]([OH:16])=O)[CH2:11][C@H:10]1[CH:12]=[CH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:29][C:30]1([S:33]([NH2:36])(=[O:35])=[O:34])[CH2:32][CH2:31]1.N12CCCN=C1CCCCC2.Cl>C1COCC1.O>[CH3:29][C:30]1([S:33]([NH:36][C:14]([C@@:9]2([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:11][C@H:10]2[CH:12]=[CH2:13])=[O:16])(=[O:35])=[O:34])[CH2:32][CH2:31]1
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참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10376443(1R,2S)-1-(((1,1-Dimethylethoxy)carbonyl)amino)-2-ethenylcyclopropanecarboxylic acidHCID 218898141-Methylcyclopropane-1-sulfonamide

생성물 1

HCID 56605353
tert-butyl [(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]carbamate
수율 74.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
85 °C

실험 절차

A round-bottom flask was charged with the carboxylic acid product of step 1 (2 g, 8.80 mmol) and 1,1′-carbonyldiimidazole (2.141 g, 13.20 mmol). Dry THF (44.0 ml) was added under anhydrous conditions and the mixture was heated (oil bath at 85° C.) for 2 hours with exclusion of moisture. The mixture was cooled to room temp and a solution of 1-methylcyclopropane-1-sulfonamide (2.379 g, 17.60 mmol) in dry THF (10 mL) was added followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (2.63 ml, 17.60 mmol). The mixture was heated (oil bath at 75° C.) overnight. The reaction mixture was treated with aq 1M HCl (20 mL) and water (50 mL). The product was extracted into ethyl acetate (400 mL) Upon separation, the organic layer was washed with aq 1M HCl/water (1:2, 80 mL), and brine (80 mL), dried over magnesium sulfate, filtered and concentrated in rotavap. The residue was purified on a gold cap RediSep® (120 g) silica gel column (gradient: 0 to 25% ethyl acetate in dichloromethane) to give the title compound (2.25 g, 6.53 mmol, 74.2% yield) as a white powder.

후처리

  1. temperatureThe mixture was cooled to room temp
  2. temperatureThe mixture was heated (oil bath at 75° C.) overnight
  3. extractionThe product was extracted into ethyl acetate (400 mL) Upon separation
  4. washthe organic layer was washed with aq 1M HCl/water (1:2, 80 mL), and brine (80 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in rotavap
  8. customThe residue was purified on a gold
  9. customcap RediSep® (120 g) silica gel column (gradient: 0 to 25% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-0e967e7a8dc24e399fe6525ff6e2c171
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09328138B2

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