Triethylamine → 1-Carbamoylmethyl-4-pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide

HRID 854008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854008
[CH3:1][CH:2]([CH3:28])[CH:3]([NH:15][C:16]([CH:18]1[CH2:22][CH:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][NH:19]1)=[O:17])[CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1.C(N(CC)CC)C.Br[CH2:37][C:38]([NH2:40])=[O:39]>C(#N)C>[CH3:1][CH:2]([CH3:28])[CH:3]([NH:15][C:16]([CH:18]1[CH2:22][CH:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][N:19]1[CH2:37][C:38](=[O:39])[NH2:40])=[O:17])[CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 696322-BromoacetamideHCID 780406994-Pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide

Produkt 1

HCID 112829251-Carbamoylmethyl-4-pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide (200 mg, 0.48 mmol, 1 equiv), in anhydrous acetonitrile (3 mL), at room temperature, under nitrogen atmosphere, was added triethylamine (0.2 mL, 1.44 mmol, 3 equiv) followed by bromoacetamide (80 mg, 0.58 mmol, 1.2 equiv). The resulting mixture was stirred at room temperature for 18 h, and evaporated to dryness. The residue obtained was first purified over silica gel, with an eluant of 7% methanolic-ammonia/dichloromethane. The desired fractions were collected, evaporated to dryness, and repurified by HPLC (to remove, the side-product from the reaction of the base with bromoacetamide). After lyophilization the desired title compound for example 40 was obtained (2.0 mg) as a white fluffy powder: HPLC: Rt=4.11 min (220.0 nm); 1H NMR (300 MHz, CD3OD) δ (rotamers) 5.46 (d, J=5.5, 1), 4.47 (dd, J=3.02, 2.7, 1.1), 4.31-4.25 (m, 3.3), 4.11 (d, J=3.02, 1.6), 2.3(s, 3), 1.65-1.52(m, 9.5), 1.12-1.09 (m, 10.3. MS (ESPOS): 476.5 [M+H]+,

Aufarbeitung

  1. customevaporated to dryness
  2. customThe residue obtained
  3. customwas first purified over silica gel, with an eluant of 7% methanolic-ammonia/dichloromethane
  4. customThe desired fractions were collected
  5. customevaporated to dryness
  6. customrepurified by HPLC (
  7. customto remove
  8. customthe side-product from the reaction of the base with bromoacetamide)

Quellen und Nachweise

ORD-Eintrag
ord-7ee4c191fa924f79b6e0dc56e43b9d53
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07256177B2

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