Hydrochloric Acid → 6-[5-(2-Oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanoylamino]hexanoic acid

HRID 1616994

Reaktionsgleichung

Reaktionsgleichung von HRID 1616994
O=C1CCC(=O)N1O[C:9](=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH:21]2[CH:17]([NH:18][C:19](=[O:22])[NH:20]2)[CH2:16][S:15]1.[NH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31].Cl>CN(C=O)C.C(=O)(O)[O-].[Na+]>[O:22]=[C:19]1[NH:18][CH:17]2[CH2:16][S:15][CH:14]([CH2:13][CH2:12][CH2:11][CH2:10][C:9]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:23])[CH:21]2[NH:20]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 5646-Aminohexanoic AcidHCID 434213NHS-Biotin

Produkt 1

HCID 51626646-[5-(2-Oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanoylamino]hexanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

5-(2-Oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (2; 0.35 g, 1.03 mmol) was completely dissolved in DMF (3 mL) with gentle warming. After cooling the 2 solution to room temperature without reprecipitation, it was mixed with a solution of ε-aminocaproic acid (0.18 g, 1.37 mmol) in sodium bicarbonate buffer (0.1 M, pH 8.0; 4 mL) while stirring. After 4 h at room temperature, the reaction mixture was acidified by HCl solution (1 N) to assist in the formation of white precipitate. The white solid was washed with cold HCl solution, dried over ether, and air-dried to afford 3 (0.30 g; 80.5%). 1H NMR (400 MHz) (DMSO) δ: 7.78 (s, 1H, CONH), 6.46 (s, 1H, CONH), 6.38 (s, 1H, CONH), 4.32 (t, 1H, CHN), 4.14 (t, 1H, CHN), 3.11 (dd, 1H, CHS), 3.02 (t, 2H, CH2NH), 2.84 (d, 1H, CHHS), 2.59 (d, 1H, CHHS), 2.18 (t, 2H, CH2COOH), 2.05 (t, 2H, CH2CO), 1.23-1.68 (m, 12H). 13C NMR (100.67 MHz) (DMSO) δ: 174.45, 171.79, 162.70, 61.03, 59.18, 55.43, 35.21, 33.60, 28.90, 28.02, 25.97, 25.33, 24.22. HRMS (ESI) calculated for C16H27N3O4S, [M+Na]+ 380.1620 (calcd.), 380.1617 (found).

Aufarbeitung

  1. customwithout reprecipitation, it
  2. washThe white solid was washed with cold HCl solution
  3. dry with materialdried over ether
  4. customair-dried
  5. customto afford 3 (0.30 g; 80.5%)

Quellen und Nachweise

ORD-Eintrag
ord-a909064667bf4a789cb5df16ac5fd2cf
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765934B2

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