2,6-Lutidine → (S)-benzyl 3-(4-(benzyloxy)phenyl)-2-(1,3-dioxoisoindolin-2-yloxy)propanoate

HRID 576880노트

반응식

HRID 576880 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@@H:16]([OH:27])[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.N1C(C)=CC=CC=1C.O[N:52]1[C:56](=[O:57])[C:55]2=[CH:58][CH:59]=[CH:60][CH:61]=[C:54]2[C:53]1=[O:62].C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([O:27][N:52]2[C:56](=[O:57])[C:55]3[C:54](=[CH:61][CH:60]=[CH:59][CH:58]=3)[C:53]2=[O:62])[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 79372,6-LutidineHCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 67749Trifluoromethanesulfonic anhydrideHCID 86663945HCID 86663945, 화합물

생성물 1

HCID 86663946(S)-benzyl 3-(4-(benzyloxy)phenyl)-2-(1,3-dioxoisoindolin-2-yloxy)propanoate수율 59.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (R)-benzyl 3-(4-(benzyloxy)phenyl)-2-hydroxypropanoate (Compound XLIII-1) 18.1 g (50.0 mmol) in dichloromethane 80 ml, trifluoromethanesulfonic anhydride 10.1 ml (60.0 mmol) and 2,6-lutidine 8.74 ml (75.0 mmol) were added and the mixture was stirred at room temperature for 0.5 hr. N-hydroxyphthalimide 8.16 g (50.0 mmol) and triethylamine 10.5 ml (75.0 mmol) were added to the reaction mixture and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and diluted with ethyl acetate 500 ml and washed with saturated sodium bicarbonate solution 500 ml, water 500 ml and brine 500 ml. The organic phase was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified on silica gel column chromatography (Merck 60N spherical, neutral elution by n-hexane:ethyl acetate=90:10 to 70:30) to obtain the title compound 15.0 g (yield 59%).

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with ethyl acetate 500 ml
  4. washwashed with saturated sodium bicarbonate solution 500 ml, water 500 ml and brine 500 ml
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified on silica gel column chromatography (Merck 60N spherical, neutral elution by n-hexane:ethyl acetate=90:10 to 70:30)

출처 및 근거

ORD 기록
ord-6971f138715e4e55a7e539739f99ce8e
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040531B2

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