Phosphorus sulfide (P2S5) → (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

HRID 1046110

반응식

HRID 1046110 반응식
[C:1]([NH:4][NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]([N:15]2[CH2:20][CH2:19][C@:18]([CH2:28][CH:29]=[CH2:30])([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[O:17][C:16]2=[O:31])[CH3:14])=[CH:9][CH:8]=1)(=O)[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:34]>C1(C)C=CC=CC=1.N1C=CC=CC=1.CCOC(C)=O>[CH2:28]([C@@:18]1([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[O:17][C:16](=[O:31])[N:15]([C@H:13]([C:10]2[CH:11]=[CH:12][C:7]([C:6]3[S:34][C:1]([CH3:2])=[N:4][N:5]=3)=[CH:8][CH:9]=2)[CH3:14])[CH2:20][CH2:19]1)[CH:29]=[CH2:30]

참가 물질

5

반응물 2

HCID 14817Phosphorus sulfide (P2S5)HCID 66857359N'-acetyl-4-((S)-1-((R)-6-allyl-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)ethyl)benzohydrazide

생성물 1

HCID 58109707(R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one수율 61%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 22007288Pyridine toluene용매

반응 조건

온도
130 °C

실험 절차

N′-acetyl-4-((S)-1-((R)-6-allyl-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)ethyl)benzohydrazide (4 mg, 0.009 mmol) was dissolved in 5:1 toluene/pyridine (1.5 mL). Phosphorus pentasulfide (8.1 mg, 2 equiv.) was added and the mixture was heated in Microwave Oven for 25 min at 130° C. LC-MS found reaction completed. The mixture was diluted with EtOAc (8 mL), washed with 5% HCl (2×5 mL), satd aq NaHCO3 solution (4 mL), brine (4 mL) and dried over Na2SO4. After filtration and concentration, the residue was purified by prep HPLC to afford 2.43 mg (61% yield). LC-MS Method 1 tR=1.7, min, m/z=438; 1H NMR (CDCl3) 7.66 (d, 2H), 7.26 (t, 2H), 7.02 (t, 2H), 6.97 (d, 2H), 5.69 (m, 2H), 5.07 (dd, 2H), 2.98 (m, 1H), 2.83 (s, 3H), 1.56 (d, 3H).

후처리

  1. customreaction
  2. washwashed with 5% HCl (2×5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by prep HPLC
  6. customto afford 2.43 mg (61% yield)

출처 및 근거

ORD 기록
ord-bbf23e15e7c449629b5c0bc77f6981db
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569292B2

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