Triethylamine → Ammonia

HRID 1866561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866561
[Si:1]([O:8][C@H:9]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:32][OH:33])[CH:26]=1)[CH2:10][NH:11][C:12]([CH3:24])([CH3:23])[CH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[Cl:65][C:66]1[CH:67]=[CH:68][C:69]([O:75][CH3:76])=[C:70]([CH2:72][CH2:73][NH2:74])[CH:71]=1>CN(C)C(=O)C>[NH3:11].[Si:1]([O:8][C@H:9]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:32][OH:33])[CH:26]=1)[CH2:10][NH:11][C:12]([CH3:23])([CH3:24])[CH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([NH:74][CH2:73][CH2:72][C:70]1[CH:71]=[C:66]([Cl:65])[CH:67]=[CH:68][C:69]=1[O:75][CH3:76])=[O:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 209848495-Chloro-2-methoxybenzeneethanamineHCID 579783093-{2-[(2R)-2-(tert-butyldimethyl silanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid

Produkt 2

HCID 222AmmoniaHCID 690233563-[2-({(2R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)-2-methylpropyl]-N-[2-(5-chloro-2-methoxyphenyl)ethyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A mixture of 3-{2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxy methylphenyl)ethylamino]-2-methylpropyl}benzoic acid (preparation 37) (400 mg, 0.85 mmol), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (320 mg, 0.85 mmol), triethylamine (225 μL, 1.6 mmol) and 2-(5-chloro-2-methoxy-phenyl)-ethylamine (preparation 70), (64 mg, 0.85 mmol) in N,N-dimethylacetamide (8 mL) was stirred for 18 hours at room temperature. The solvent was removed in vacuo and the residue was partitioned between dichloromethane (4 mL) and saturated sodium hydrogen carbonate solution (1 mL). The organic solution was then dried over magnesium sulfate, concentrated in vacuo and the residue was purified using an ISCO Companion® silica cartridge, eluting with dichloromethane:methanol:0.88 ammonia, 90:10:1 to 80:20:2, to afford the title compound in 22% yield.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between dichloromethane (4 mL) and saturated sodium hydrogen carbonate solution (1 mL)
  3. dry with materialThe organic solution was then dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified
  6. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-d589937ccd834c09bdc44c1bcf609949
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629358B2

Notizen zur Reaktion

Wird geladen…