Methyl chloroformate → Methyl 3-cyano-4-(isopropylsulfonyl)phenylcarbamate

HRID 1667611노트

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HRID 1667611 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].Cl[C:17]([O:19][CH3:20])=[O:18]>N1C=CC=CC=1>[C:7]([C:6]1[CH:9]=[C:2]([NH:1][C:17](=[O:18])[O:19][CH3:20])[CH:3]=[CH:4][C:5]=1[S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])#[N:8]

참가 물질

4

반응물 2

HCID 6586Methyl chloroformateHCID 574482075-Amino-2-(isopropylsulfonyl)benzonitrile

생성물 1

HCID 57448208Methyl 3-cyano-4-(isopropylsulfonyl)phenylcarbamate수율 88%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
0 °C

실험 절차

To 15C (450 mg, 2 mmol) in pyridine (10 mL) at 0° C. was added methyl chloroformate (0.8 mL, 10 mmol). The reaction was stirred at 0° C. for 20 min, then warmed to rt for 2 h. The reaction was concentrated, then diluted with ethyl acetate, washed with brine, dried (Na2SO4), filtered and concentrated. The resulting residue was purified via silica gel chromatography (0-60% ethyl acetate/hexanes) to provide 15D (490 mg, 88%). LC-MS: 283.35 (M+H)+.

후처리

  1. temperaturewarmed to rt for 2 h
  2. concentrationThe reaction was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified via silica gel chromatography (0-60% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-8b6db5b81d474600a0ed62124ad27042
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044242B2

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