Triphenylphosphine → 3-[2-Oxo-3-(1,2,3-trimethyl-1H-indol-7-ylmethyl)-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl ester

HRID 1747364노트

반응식

HRID 1747364 반응식
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])[CH3:2].[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[CH2:31]O)[C:24]([CH3:33])=[C:23]1[CH3:34].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:31][C:29]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:30]=2[N:22]([CH3:21])[C:23]([CH3:34])=[C:24]3[CH3:33])[C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])[CH3:2]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 594972633-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterHCID 59497596HCID 59497596, 화합물

생성물 1

HCID 594972503-[2-Oxo-3-(1,2,3-trimethyl-1H-indol-7-ylmethyl)-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl ester수율 49.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (100 mg, 0.36 mmol) in THF (10 mL) were added (1,2,3-Trimethyl-1H-indol-7-yl)-methanol (103 mg, 0.54 mmol), DIAD (diisoproyl azo-dicarboxylate) (0.14 mL, 0.7 mmol) and triphenylphosphine (95 mg, 0.36 mmol) at room temperature. The solution was stirred at the same temperatrue for 12 hours. The solution was filtered and the filtrate was concentrated. The residue was purified by combFlash with 10% EtOAc in Hexane as the eluent to afford the desirable product 3-[2-Oxo-3-(1,2,3-trimethyl-1H-indol-7-ylmethyl)-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl ester (80 mg, 49%) as a white foam.

후처리

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by combFlash with 10% EtOAc in Hexane as the eluent

출처 및 근거

ORD 기록
ord-bdec2d67ad4549ec9740231c4437a360
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150556B2

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