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

HRID 1942821

Reaktionsgleichung

Reaktionsgleichung von HRID 1942821
[CH3:1][Si:2]([CH2:5][N:6]1[CH:10]=[C:9]([CH2:11][NH:12][CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)[N:8]=[N:7]1)([CH3:4])[CH3:3].C(Cl)Cl.CCN(CC)CC.[C:34](Cl)(=[O:36])[CH3:35]>CCOC(C)=O>[C:34]([N:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=1)[CH2:11][C:9]1[N:8]=[N:7][N:6]([CH2:5][Si:2]([CH3:3])([CH3:1])[CH3:4])[CH:10]=1)(=[O:36])[CH3:35]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59627278Methyl 4-{[({1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amino]methyl}benzoate

Produkt 1

HCID 59627274Methyl 4-{[acetyl({1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amino]methyl}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of methyl 4-{[({1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amino]methyl}benzoate (133 mg, 400 mmol), DCM (1.33 mL) and Et3N (167 uL, 1.2 mmol) were treated with acetyl chloride (42.7 uL, 0.600 mmol) and stirred for 5 min. The reaction was diluted with EtOAc and washed with 2M aq. HCl, water, brine, dried (MgSO4) and concentrated to afford the requisite compound as a clear, colorless residue. MS: cal'd 375 (MH+), exp 375 (MH+).

Aufarbeitung

  1. washwashed with 2M aq. HCl, water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto afford the requisite compound as a clear, colorless residue

Quellen und Nachweise

ORD-Eintrag
ord-2115f23c5cbf4c46aeb7150ab72f9f6a
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389553B2

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