Sodium hydride → HCID 71477845, Verbindung

HRID 707785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 707785
[Br:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5]([Br:11])=[C:4]([Br:12])[C:3]=1[Br:13].[H-].[Na+].C[O:17][C:18](=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br>CN(C=O)C>[Br:11][C:5]1[C:6]2[N:7]=[CH:8][N:9]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18]([OH:27])=[O:17])[C:10]=2[C:2]([Br:1])=[C:3]([Br:13])[C:4]=1[Br:12]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 51497394,5,6,7-tetrabromobenzimidazoleHCID 11107373Methyl 8-bromooctanoate

Produkt 1

HCID 71477845HCID 71477845, VerbindungAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4,5,6,7-tetrabromo-1H-benzimidazole (115 mg, 0.26 mmol) and NaH suspension (12 mg, ˜0.28 mmol) were stirred in DMF for 30 min and then 8-bromooctanoic acid methyl ester (182 mg, 0.77 mmol) was added. The solution was stirred for 2 days and then evaporated to dryness. The residue was purified by flash chromatography (CHCl3: methanol; 20:1 by volume). The methyl ester was hydrolyzed in the mixture of methanol and aqueous KOH for 1 hour and the solvents were removed in vacuum. The obtained residue was partitioned between ethyl acetate and KHSO4, the organic layer was dried and evaporated to yield 8-(4,5,6,7-tetrabromo-1H-benzimidazole-1-yl)octanoic acid (95 mg, 62% over two steps). 1H NMR (200 MHz; DMSO6d; Me4Si) 1.28 (m, 6H), 1.48 (m, 2H), 1.76 (m, 2H), 2.19 (t, J=7.3 Hz, 2H), 4.48 (t, J=7.6 Hz, 2H), 8.51 (s, 1H), 11.91 (br, 1H). 13C NMR (50 MHz; DMSO6d; Me4Si) 24.3, 25.5, 28.1, 28.3, 31.5, 33.6, 46.4, 106.5, 116.6, 120.4, 122.3, 131.3, 143.7, 148.9, 174.4. B. Synthesis of TBBI-OcA-(D-Asp)-(L-Asp)5-(L-Lys)-OH

Aufarbeitung

  1. customevaporated to dryness
  2. customThe residue was purified by flash chromatography (CHCl3: methanol; 20:1 by volume)
  3. additionThe methyl ester was hydrolyzed in the mixture of methanol and aqueous KOH for 1 hour
  4. customthe solvents were removed in vacuum
  5. customThe obtained residue was partitioned between ethyl acetate and KHSO4
  6. customthe organic layer was dried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-40651a3e1a18491aa2aa36b14c897353
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09176064B2

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