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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-butyl 4-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216905
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HRID 216905 반응식
NC(=O)[C@@H](NC(C1(NC(=O)OC(C)(C)C)CCOCC1)=O)CC1C=CC(C2C=CC(C(F)(F)F)=CC=2)=CC=1.[NH2:39][C:40](=O)[C@@H:41]([NH:60][C:61]([C:63]1([NH:69][C:70](=[O:76])[O:71][C:72]([CH3:75])([CH3:74])[CH3:73])[CH2:68][CH2:67][O:66][CH2:65][CH2:64]1)=[O:62])[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([S:55]([CH2:58][CH3:59])(=[O:57])=[O:56])=[CH:51][CH:50]=2)=[CH:45][CH:44]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClCCl>[C:40]([C@@H:41]([NH:60][C:61]([C:63]1([NH:69][C:70](=[O:76])[O:71][C:72]([CH3:75])([CH3:74])[CH3:73])[CH2:68][CH2:67][O:66][CH2:65][CH2:64]1)=[O:62])[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([S:55]([CH2:58][CH3:59])(=[O:57])=[O:56])=[CH:51][CH:50]=2)=[CH:45][CH:44]=1)#[N:39]
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참가 물질

5

반응물 3

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568598(S)-tert-butyl 4-(1-amino-1-oxo-3-(4'-(trifluoromethyl)biphenyl-4-yl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateHCID 59568601(S)-tert-butyl 4-(1-amino-3-(4'-(ethylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

생성물 1

HCID 59568561(S)-tert-butyl 4-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The mixture of (S)-tert-butyl 4-(1-amino-1-oxo-3-(4′-(trifluoromethyl)biphenyl-4-yl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate and (S)-tert-butyl 4-(1-amino-3-(4′-(ethylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iv), 1.7 g) in dichloromethane (15 mL) was treated with Burgess' reagent (1.19 g) and the mixture was stirred at room temperature for 72 h. The reaction was evaporated onto silica and purified on a silica column eluting with 20% ethyl acetate in isohexane, then 50% ethyl acetate in isohexane and finally 100% ethyl acetate to afford after evaporation of the relevant fractions (S)-tert-butyl 4-(1-cyano-2-(4′-(trifluoromethyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (650 mg) and (S)-tert-butyl 4-(1-cyano-2-(4′-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (920 mg).

후처리

  1. customThe reaction was evaporated onto silica
  2. custompurified on a silica column
  3. washeluting with 20% ethyl acetate in isohexane
  4. custom50% ethyl acetate in isohexane and finally 100% ethyl acetate to afford
  5. customafter evaporation of the relevant fractions (S)-tert-butyl 4-(1-cyano-2-(4′-(trifluoromethyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (650 mg) and (S)-tert-butyl 4-(1-cyano-2-(4′-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (920 mg)

출처 및 근거

ORD 기록
ord-52e35b59fc9f4f55a3495e97bf1c4c39
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08193239B2

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