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Pyridine → (S)-2-{acetyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methylbutyric acid

HRID 854655
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 854655
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:11][CH:12]([CH3:44])[C@H:13]([NH:21][CH2:22][C@H:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([O:29][CH2:30][C:31]2[N:32]=[C:33]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)[O:34][C:35]=2[CH3:36])[CH2:24]1)[C:14]([O:16]C(C)(C)C)=[O:15]>ClCCl.O>[C:1]([N:21]([CH2:22][C@H:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([O:29][CH2:30][C:31]2[N:32]=[C:33]([C:37]3[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][CH:42]=3)[O:34][C:35]=2[CH3:36])[CH2:24]1)[C@@H:13]([CH:12]([CH3:44])[CH3:11])[C:14]([OH:16])=[O:15])(=[O:3])[CH3:2]
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Komponenten

6

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86597944tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyrate

Produkt 1

HCID 69240762(S)-2-{acetyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methylbutyric acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

12 μl of acetyl chloride and 22 μl of pyridine are added to 40 mg of tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyrate in 0.5 ml of dichloromethane, and the mixture is stirred at room temperature for 18 h. The solution is then diluted with water and dichloromethane, the aqueous phase is removed and extracted with dichloromethane and the combined phases are dried over MgSO4 and concentrated. The residue is taken up in 0.5 ml of trifluoroacetic acid and allowed to stand at room temperature overnight. The solvent is distilled off completely and the residue is purified by HPLC, which gives 17 mg of (S)-2-{acetyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methylbutyric acid. C26H36N2O5 (456.59); LCMS (ESI): 457.36 (MH+).

Aufarbeitung

  1. customthe aqueous phase is removed
  2. extractionextracted with dichloromethane
  3. dry with materialthe combined phases are dried over MgSO4
  4. concentrationconcentrated
  5. waitto stand at room temperature overnight
  6. distillationThe solvent is distilled off completely
  7. customthe residue is purified by HPLC, which

Quellen und Nachweise

ORD-Eintrag
ord-ff110fff65a849a78a16d274d5843534
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07259177B2

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