Triphenylphosphine → Methyl 4-{[[(2,4-dinitrophenyl)sulfonyl]({1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amino]methyl}benzoate

HRID 1942819

Reaktionsgleichung

Reaktionsgleichung von HRID 1942819
[CH3:1][Si:2]([CH2:5][N:6]1[CH:10]=[C:9]([CH2:11]O)[N:8]=[N:7]1)([CH3:4])[CH3:3].[N+:13]([C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[S:25]([NH:28][CH2:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1)(=[O:27])=[O:26])([O-:15])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>CCOC(C)=O.C1C=CC=CC=1>[N+:13]([C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[S:25]([N:28]([CH2:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1)[CH2:11][C:9]1[N:8]=[N:7][N:6]([CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[CH:10]=1)(=[O:26])=[O:27])([O-:15])=[O:14]

Komponenten

7

Edukt 4

HCID 11776Triphenylphosphine2×HCID 5462977Diethyl azodicarboxylate2×HCID 59627317(1-((Trimethylsilyl)methyl)-1h-1,2,3-triazol-4-yl)methanolHCID 59627340Methyl 4-({[(2,4-dinitrophenyl)sulfonyl]amino}methyl)benzoate

Produkt 1

HCID 59627272Methyl 4-{[[(2,4-dinitrophenyl)sulfonyl]({1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amino]methyl}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of {1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methanol (241 mg, 1.30 mmol), methyl 4-({[(2,4-dinitrophenyl)sulfonyl]amino}methyl)benzoate (514 mg, 1.30 mmol), triphenylphosphine (409 mg, 1.56 mmol) and benzene (4.34 mL) was treated with diethylazodicarboxylate (247 uL, 1.56 mmol). After one hour additional portions of triphenylphosphine (204 mg, 0.780 mmol) and diethylazodicarboxylate (124 uL, 0.780 mmol) The reaction was diluted with EtOAc and washed with 2M aq. HCl 2×, water, brine, dried (MgSO4) and concentrated to afford a brown oil used crude in the next reaction. MS: cal'd 563 (MH+), exp 563 (MH+).

Aufarbeitung

  1. washwashed with 2M aq. HCl 2×, water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto afford a brown oil
  5. customin the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-6535ea6dada64804aaef98daa3cf0d04
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389553B2

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