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Diisopropylethylamine → methyl (N-tert-butoxycarbonyl-6-aminohexanoyl)aminomethyl-2,6-dihydroxybenzoate

HRID 1417596
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1417596
Cl.NC[C:4]1[CH:13]=[C:12]([OH:14])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:15])[CH:5]=1.[CH:16]([N:19](CC)C(C)C)(C)C.C1(=O)N(O[C:31](=[O:45])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])C(=O)CC1>CN(C)C=O>[C:41]([O:40][C:38]([NH:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][C:31]([NH:19][CH2:16][C:13]1[C:12]([OH:14])=[C:7]([C:6]([OH:15])=[CH:5][CH:4]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:45])=[O:39])([CH3:42])([CH3:43])[CH3:44]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5074016Boc-6-Ahx-OSuHCID 22556072Methyl 4-aminomethyl-2,6-dihydroxybenzoate hydrochloride

Produkt 1

HCID 86753339methyl (N-tert-butoxycarbonyl-6-aminohexanoyl)aminomethyl-2,6-dihydroxybenzoateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

Methyl 4-aminomethyl-2,6-dihydroxybenzoate hydrochloride (1.50 grams, 6.4 mmoles) was suspended in anhydrous N,N-dimethylformamide (25 mL), and N,N-diisopropylethylamine (2.2 mL, 12.8 mmoles) was added, followed by N-tert-butoxycarbonyl-6-aminohexanoic acid succinimidyl ester (2.10 grams, 6.4 mmoles). The mixture was stirred under dry nitrogen for 4 hours, during which time all solids dissolved. The solvent was then evaporated to leave a light brown syrup, which was partitioned between ethyl acetate (70 mL) and 1M aqueous hydrochloric acid (50 mL). The layers were separated, and the ethyl acetate solution was washed with saturated aqueous sodium bicarbonate (50 mL) and saturated aqueous sodium chloride (50 mL). The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered, and evaporated to an amorphous off-white solid. The solid was crystallized from ethyl acetate/hexanes, filtered, and dried in vacuo to afford 2.10 grams (80% yield) of methyl (N-tert-butoxycarbonyl-6-aminohexanoyl)aminomethyl-2,6-dihydroxybenzoate (m.p. 73°-76° C., open capillary, uncorrected).

Aufarbeitung

  1. dissolutiondissolved
  2. customThe solvent was then evaporated
  3. customto leave a light brown syrup, which
  4. customwas partitioned between ethyl acetate (70 mL) and 1M aqueous hydrochloric acid (50 mL)
  5. customThe layers were separated
  6. washthe ethyl acetate solution was washed with saturated aqueous sodium bicarbonate (50 mL) and saturated aqueous sodium chloride (50 mL)
  7. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated to an amorphous off-white solid
  10. customThe solid was crystallized from ethyl acetate/hexanes
  11. filtrationfiltered
  12. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-861c8abadfa14d6195a941116c03e240
Quelldatensatz
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05877297

Notizen zur Reaktion

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