Dicyclohexylcarbodiimide → 5-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid mono-tert-butyl ester

HRID 562526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 562526
[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].C1C=NC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:50]([O:54][C:55](=[O:66])[C:56]1[CH:64]=[C:63]([NH2:65])[CH:62]=[C:58]([C:59]([OH:61])=[O:60])[CH:57]=1)([CH3:53])([CH3:52])[CH3:51].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:50]([O:54][C:55](=[O:66])[C:56]1[CH:64]=[C:63]([NH:65][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])[CH:62]=[C:58]([C:59]([OH:61])=[O:60])[CH:57]=1)([CH3:53])([CH3:51])[CH3:52]

Komponenten

7

Edukt 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 5781772316-(Tert-butoxy)-16-oxohexadecanoic acidHCID 866192463-Amino-5-(tert-butoxycarbonyl)benzoic acid

Produkt 1

HCID 667245005-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid mono-tert-butyl esterAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of hexadecandioic acid mono t-butyl ester (100 mg, 0.29 mmol) in dry DCM (2 ml), HOAt (44 mg, 0.29 mmol) and DCC (72 mg, 32 mmol) was added. The mixture was stirred at 50° C. for 1 h. The oil bath was removed. 5-Amino-isophthalic acid mono t-butyl ester (69 mg, 0.29) and DIPEA (0.07 ml, 0.32 mmol) was added. The mixture was stirred at RT over night under nitrogen. The yellow suspension was filtered and the filtrate was concentrated. The residue was redissolved in EtOAc and extracted with 0.1 N HCl (2×), brine (1×), dried (Na2SO4) and concentrated to give a white solid, which was purified twice by flash chromatography using EtOAc/Hept 1:2+5% AcOH. The title compound was obtained in 86% yield (0.140 g) as an oil containing an impurity.

Aufarbeitung

  1. customThe oil bath was removed
  2. stirringThe mixture was stirred at RT over night under nitrogen
  3. filtrationThe yellow suspension was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was redissolved in EtOAc
  6. extractionextracted with 0.1 N HCl (2×), brine (1×)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customto give a white solid, which
  10. customwas purified twice by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4b5b0a7414874d18a59d8de006a4e6f7
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067362B2

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