Diisopropylethylamine → (R)-2-(4-methoxy-4-oxobutanamido)-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoic acid

HRID 388165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 388165
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3][C:4]([O-:6])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH3:43][C:44]([CH3:64])=[CH:45][CH2:46][CH2:47]/[C:48](/[CH3:63])=[CH:49]/[CH2:50][CH2:51]/[C:52](/[CH3:62])=[CH:53]/[CH2:54][S:55][CH2:56][C@H:57]([NH2:61])[C:58]([OH:60])=[O:59]>C1COCC1.C(OCC)(=O)C>[CH3:9][O:8][C:1](=[O:7])[CH2:2][CH2:3][C:4]([NH:61][C@@H:57]([CH2:56][S:55][CH2:54]/[CH:53]=[C:52](\[CH3:62])/[CH2:51][CH2:50]/[CH:49]=[C:48](\[CH3:63])/[CH2:47][CH2:46][CH:45]=[C:44]([CH3:64])[CH3:43])[C:58]([OH:60])=[O:59])=[O:6]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 6438372FarnesylcysteineHCID 6930703Mono-Methyl SuccinateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 46208613(R)-2-(4-methoxy-4-oxobutanamido)-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a 100 mL round bottom flask, mono-methyl succinate (132 mg, 1 mmol), 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.1 mg, 1.1 mmol) and N,N-diisopropyl-ethyl-amine (0.52 mL, 3 mmol) were mixed in THF (5 mL). The reaction solution was stirred at room temperature for ten minutes. S-trans, trans-Farnesyl-L-cysteine (325 mg, 1 mmol) was added to reaction mixture. The reaction solution was stirred at room temperature overnight. Ethyl acetate (50 mL) was added and then washed with saturated ammonium chloride aqueous solution (20 mL×2), DI water (20 mL×2) and brine (20 mL×2) sequentially. The ethyl acetate solution was dried by Na2SO4 and concentrated in vacuo to afford a crude Compound N-17. The crude Compound N-17 was purified by HPLC (110 mg, 25%) to yield Compound N-17. 1H-NMR (500 MHz, MeOH-d4): δ 1.50 (s, 6H), 1.57 (s, 3H), 1.58 (s, 3H), 1.85-1.88 (m, 2H), 1.91-1.96 (m, 4H), 1.99-2.03 (m, 2H), 2.46-2.54 (m, 4H), 2.68 (dd, J=7.5, 13.5 Hz, 1H), 2.90 (dd, J=4.5, 13.5 Hz, 1H), 3.09-3.12 (m, 2H), 3.21 (s, 3H), 4.35 (dd, J=4.5, 7.0 Hz, 1H), 4.98-5.02 (m, 2H), 5.14 (t, J=7.5 Hz, 1H). 13C-NMR (125 MHz, MeOH-d4): δ 16.12, 16.25, 17.79, 25.94, 27.48, 27.79, 30.40, 30.69, 31.73, 35.49, 40.77, 40.89, 52.24, 55.45, 121.82, 125.22, 125.47, 132.08, 136.15, 139.97, 173.57, 174.80, 177.17; ES-MS: mass calcd for Chemical Formula: C23H37NO5S 439.2. Found (M+Na) m/z 462.2.

Aufarbeitung

  1. stirringThe reaction solution was stirred at room temperature overnight
  2. washwashed with saturated ammonium chloride aqueous solution (20 mL×2), DI water (20 mL×2) and brine (20 mL×2) sequentially
  3. dry with materialThe ethyl acetate solution was dried by Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d08c472fb12d4a669cc366044604f10b
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372884B2

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