Diisopropylethylamine → 4-{[(2-tert-Butoxycarbonylethyl)-(15-tert-butoxycarbonyl-pentadecanoyl)amino]methyl}benzoic acid

HRID 562516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 562516
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=O)([CH3:4])([CH3:3])[CH3:2].ON1C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[C:44]([O:48][C:49]([CH2:51][CH2:52][NH:53][CH2:54][C:55]1[CH:63]=[CH:62][C:58]([C:59]([OH:61])=[O:60])=[CH:57][CH:56]=1)=[O:50])([CH3:47])([CH3:46])[CH3:45]>C(OCC)(=O)C>[C:44]([O:48][C:49]([CH2:51][CH2:52][N:53]([CH2:54][C:55]1[CH:63]=[CH:62][C:58]([C:59]([OH:61])=[O:60])=[CH:57][CH:56]=1)[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:24])=[O:50])([CH3:47])([CH3:45])[CH3:46]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 5781772316-(Tert-butoxy)-16-oxohexadecanoic acidHCID 596879094-[(2-tert-Butoxycarbonylethylamino)methyl]benzoic acid

Produkt 1

HCID 580794854-{[(2-tert-Butoxycarbonylethyl)-(15-tert-butoxycarbonyl-pentadecanoyl)amino]methyl}benzoic acidAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Hexadecanedioic acid mono-tert-butyl ester (0.3 g, 0.88 mmol) was dissolved in ethyl acetate. N-Ethyl-N-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.167 g, 0.88 mmol) and 1-hydroxy-7-azabenzotriazole (0.119 g, 0.88 mmol) was added and the mixture was stirred at 50° C. for 1 hour. After cooling to room temperature, diisopropylethylamin (0.45 mL, 2.63 mmol) was added followed by 4-[(2-tert-Butoxycarbonylethylamino)methyl]benzoic acid (0.489 g, 1.75 mmol). The mixture was stirred overnight under nitrogen at room temperature. The mixture was separated between ethyl acetate (100 mL) and water (2×50 mL). The organic phase was dried (Na2SO4), solvent removed in vacuo. The crude product was purified by RP-HPLC on C18-column, buffer A: 0.1% TFA, buffer B: MeCN+0.1% TFA; gradient 80-100% B to yield the title compound (145 mg, 27%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. stirringThe mixture was stirred overnight under nitrogen at room temperature
  3. customThe mixture was separated between ethyl acetate (100 mL) and water (2×50 mL)
  4. dry with materialThe organic phase was dried (Na2SO4), solvent
  5. customremoved in vacuo
  6. customThe crude product was purified by RP-HPLC on C18-column, buffer A: 0.1% TFA, buffer B

Quellen und Nachweise

ORD-Eintrag
ord-230d886d718d4433b31ee465c2799511
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067362B2

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