Lithium Hydroxide → 4-({Acetyl[(1-methyl-1H-1,2,3-triazol-4-yl)methyl]amino}methyl)benzoic acid

HRID 1942822

Reaktionsgleichung

Reaktionsgleichung von HRID 1942822
[C:1]([N:4]([CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=1)[CH2:5][C:6]1[N:7]=[N:8][N:9]([CH2:11][Si](C)(C)C)[CH:10]=1)(=[O:3])[CH3:2].C1COCC1.[Li+].[OH-]>CO>[C:1]([N:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=1)[CH2:5][C:6]1[N:7]=[N:8][N:9]([CH3:11])[CH:10]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59627274Methyl 4-{[acetyl({1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amino]methyl}benzoate

Produkt 1

HCID 596272824-({Acetyl[(1-methyl-1H-1,2,3-triazol-4-yl)methyl]amino}methyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methyl 4-{[acetyl({1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amino]methyl}benzoate (101 mg, 0.270 mmol), THF (809 uL) and MeOH (270 uL) was treated with aqueous LiOH (270 uL, 0.809 mmol, 3M in water). The reaction immediately turned red and was stirred overnight. The reaction was quenched with 2M aq. HCl and extracted with EtOAc 2×. The combined organic layers were washed with brine, dried (MgSO4) and concentrated to afford the protosilylated carboxylic acid as a yellow oil. MS: cal'd 361 (MH+), exp 361 (MH+).

Aufarbeitung

  1. customThe reaction immediately turned red
  2. customThe reaction was quenched with 2M aq. HCl
  3. extractionextracted with EtOAc 2×
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-725f0b4eb416433d9b7c3d556a0d6e02
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389553B2

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