Triphenylphosphine → Methyl 2-(4-(2-((1S,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)ethoxy)phenyl)acetate

HRID 1850776노트

반응식

HRID 1850776 반응식
[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][CH2:19][OH:20])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].O[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C([O-])=O)=NC([O-])=O>C1COCC1.C(Cl)Cl>[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][CH2:19][O:20][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:24][CH:23]=3)[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 51573101N-carboxylatoiminocarbamateHCID 708186512-((1S,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)ethanol

생성물 1

HCID 70856387Methyl 2-(4-(2-((1S,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)ethoxy)phenyl)acetate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

2-((1S,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)ethanol (1.7 g, 6.08 mmol), methyl 2-(4-hydroxyphenyl)acetate (1.5 g, 9.1 mmol) and triphenylphosphine (2.4 g, 9.1 mmol) were dissolved in THF (30 ml). The mixture was stirred at RT under N2 for 5 min and disisopropyl azodicarboxylate (1.78 ml, 9.1 mmol) was added. The mixture was stirred at RT overnight. The mixture was diluted with DCM (50 ml), washed with water, dried and evaporated. The crude material was purified by silica gel column (100 g SNAP, 5-25% EtOAc in hexane) to afford the desired product. LC/MS (m/z): 428 (M+H)+.

후처리

  1. stirringThe mixture was stirred at RT overnight
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customThe crude material was purified by silica gel column (100 g SNAP, 5-25% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-c35a73d19db349ba9ac312d0cb41313f
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957062B2

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