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Triphenylphosphine → HCID 71606413, 화합물

HRID 2207470
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HRID 2207470 반응식
[CH3:1][O:2][C:3]1[C:30]([O:31][CH2:32][CH2:33][CH2:34][C:35]([NH:37][C:38]2[CH:42]=[C:41]([C:43](=[O:61])[NH:44][C:45]3[CH:50]=[CH:49][C:48]([C:51]4[CH:55]=[C:54]([C:56]([O:58][CH3:59])=[O:57])[N:53]([CH3:60])[CH:52]=4)=[CH:47][CH:46]=3)[N:40]([CH3:62])[CH:39]=2)=[O:36])=[CH:29][C:6]2[N:7](C(OCC=C)=O)[C@@H:8](OC3CCCCO3)[C@@H:9]3[CH2:15][CH2:14][CH2:13][N:10]3[C:11](=[O:12])[C:5]=2[CH:4]=1.N1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]1[C:30]([O:31][CH2:32][CH2:33][CH2:34][C:35]([NH:37][C:38]2[CH:42]=[C:41]([C:43]([NH:44][C:45]3[CH:50]=[CH:49][C:48]([C:51]4[CH:55]=[C:54]([C:56]([O:58][CH3:59])=[O:57])[N:53]([CH3:60])[CH:52]=4)=[CH:47][CH:46]=3)=[O:61])[N:40]([CH3:62])[CH:39]=2)=[O:36])=[CH:29][C:6]2[N:7]=[CH:8][C@@H:9]3[CH2:15][CH2:14][CH2:13][N:10]3[C:11](=[O:12])[C:5]=2[CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11776TriphenylphosphineHCID 31268PyrrolidineHCID 131735922(11S,11aS)-allyl 7-methoxy-8-(4-((5-((4-(5-(methoxycarbonyl)-1-methyl-1H-pyrrol-3-yl)phenyl)carbamoyl)-1-methyl-1H-pyrrol-3-yl)amino)-4-oxobutoxy)-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate

생성물 1

HCID 71606413HCID 71606413, 화합물수율 34.3%

시약·촉매·용매

2
HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6344Dichloromethane용매

실험 절차

Palladium tetrakis[triphenylphosphine](12.17 mg, 10.5 μM, 0.05 equiv) was added to a solution of Alloc-THP-PBD conjugate 15e (179 mg, 0.21 mmol), pyrrolidine (17.91 mg, 0.25 mmol, 1.2 eq) and triphenylphosphine (13.81 mg, 0.25 equiv) in DCM (5 mL). The reaction mixture was stirred at room temperature for 2 h at which point TLC showed completion of reaction. Excess DCM was removed by rotary evaporation under reduced pressure and the resulting residue dried in vacuo to remove pyrrolidone. The product was purified by high performance liquid chromatography (eluted with acetone:water gradient with 1% TFA) to give the product as a light yellowish solid, 16e (48 mg, 34% after HPLC purification).

후처리

  1. customcompletion of reaction
  2. customExcess DCM was removed by rotary evaporation under reduced pressure
  3. customthe resulting residue dried in vacuo
  4. customto remove pyrrolidone
  5. customThe product was purified by high performance liquid chromatography (eluted with acetone:water gradient with 1% TFA)

출처 및 근거

ORD 기록
ord-74358d3c79f74639bcd1eb6b246b01d0
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09376440B2

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