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Triphenylphosphine → HCID 178498319, 화합물

HRID 1627294
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HRID 1627294 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([O:24][CH3:25])[CH:18]=3)[C:15]([S:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([CH2:38][CH2:39][CH2:40]O)=[C:32]([CH:37]=3)[C:33]([O:35][CH3:36])=[O:34])=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:42][C:43](=[N:52]C(=O)OC(C)(C)C)[NH:44]C(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([O:24][CH3:25])[CH:18]=3)[C:15]([S:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([CH2:38][CH2:39][CH2:40][NH:44][C:43]([NH2:52])=[NH:42])=[C:32]([CH:37]=3)[C:33]([O:35][CH3:36])=[O:34])=[N:14][CH:13]=2)([CH3:10])[CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8]
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참가 물질

6

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HCID 11776TriphenylphosphineHCID 4124838N,N'-Di-Boc-guanidineHCID 5363146Diisopropyl azodicarboxylateHCID 66740842Methyl 5-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluoro-3-methoxyphenyl)-1H-imidazol-2-ylthio)methyl)-2-(3-hydroxypropyl)benzoate

생성물 1

HCID 178498319HCID 178498319, 화합물수율 77.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of methyl 5-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluoro-3-methoxyphenyl)-1H-imidazol-2-ylthio)methyl)-2-(3-hydroxypropyl)benzoate (90 mg, 0.15 mmol, 1.0 eq), tert-butyl amino(tert-butoxycarbonylamino)methylenecarbamate (76 mg, 0.29 mmol, 2.0 eq) and triphenylphosphine (59 mg, 0.22 mmol, 1.5 eq) in tetrahydrofuran (0.7 mL) was added diisopropylazodicarboxylate (0.04 mL, 0.22 mmol, 1.5 eq). After stirring for 16 h, the reaction mixture was directly poured onto silica gel and purified (0 to 75% ethyl acetate/hexanes). This product was treated with 1:2 trifluoroacetic acid/dichloromethane (2 mL) at room temperature for 16 h. The reaction mixture was concentrated to provide 77 mg (70%) of methyl 5-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluoro-3-methoxyphenyl)-1H-imidazol-2-ylthio)methyl)-2-(3-guanidinopropyl)benzoate: MS (EI) m/z 759 [(M-Boc)H+].

후처리

  1. additionthe reaction mixture was directly poured onto silica gel
  2. custompurified (0 to 75% ethyl acetate/hexanes)
  3. additionThis product was treated with 1:2 trifluoroacetic acid/dichloromethane (2 mL) at room temperature for 16 h
  4. concentrationThe reaction mixture was concentrated

출처 및 근거

ORD 기록
ord-3bcee7772342462d9c6687935f0f5aee
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785488B2

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