Ammonia → HCID 58109425, 화합물

HRID 2037533노트

반응식

HRID 2037533 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@@:20]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)([CH2:23][CH2:24][OH:25])[O:19][C:18]2=[O:33])[CH3:16])=[CH:11][CH:10]=1.[C:34](Cl)(=[O:45])OC1C=CC([N+]([O-])=O)=CC=1.[NH3:47]>C(Cl)Cl>[C:34](=[O:45])([O:25][CH2:24][CH2:23][C@@:20]1([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[O:19][C:18](=[O:33])[N:17]([C@H:15]([C:12]2[CH:13]=[CH:14][C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[CH:10][CH:11]=2)[CH3:16])[CH2:22][CH2:21]1)[NH2:47]

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 821294-Nitrophenyl chloroformateHCID 53361128HCID 53361128, 화합물

생성물 1

HCID 58109425HCID 58109425, 화합물수율 35%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (50 mg, 0.11 mmol) was dissolved in CH2Cl2 (3 mL), followed by the addition of TEA (1 mL) and 4-nitrophenyl carbonochloridate (88 mg, 0.44 mmol). The mixture was stirred at rt overnight. Aqueous ammonia (2 mL) was added and the mixture was stirred at rt for 3 h. After separation of the water layer, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to give the crude product, which was purified by preparative TLC to afford 2-((S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl carbamate (20 mg, 35%). LC-MS Method 3 tR=1.36, min, m/z=499; 1H NMR (CDCl3): 1.48 (m, 3H), 2.14-2.33 (m, 5H), 2.91 (m, 1H), 3.42 (s, 1H), 3.95 (m, 1H), 4.07 (m, 1H), 4.62 (s, 2H), 5.61 (m, 1H), 6.79-7.01 (m, 6H), 7.23 (m, 5H).

후처리

  1. stirringthe mixture was stirred at rt for 3 h
  2. customAfter separation of the water layer
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product, which
  7. customwas purified by preparative TLC

출처 및 근거

ORD 기록
ord-963c0d976b854e4ea8f867d4cbfbd9ca
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575156B2

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