Pyridine → (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl fluoride

HRID 1396855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1396855
[CH:1]1([CH2:6][C@H:7]([CH2:11][N:12]([CH:21]=[O:22])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:23]C1N=C(F)N=C(F)N=1.N1C=CC=CC=1>ClCCl>[CH:1]1([CH2:6][C@H:7]([CH2:11][N:12]([CH:21]=[O:22])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]([F:23])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 21305218(R)-3-(Benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acid

Produkt 1

HCID 86706340(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl fluoride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (as prepared in Scheme 1; also described in WO 2009061879) (5.2 g, 17.03 mmol) dissolved in dichloromethane (DCM) (75 mL) was added 2,4,6-trifluoro-1,3,5-triazine (1.5 mL, 17.9 mmol) followed by pyridine (1.51 mL, 18.7 mmol). The reaction mixture was stirred at 25° C. for 2 h, and then the reaction mixture was diluted with DCM (100 mL) and washed (1×50 mL) with 5% citric acid followed by 50 mL of sat. NaHCO3. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl fluoride as a pale yellow oil. LC-MS (ES) m/e 306.8 (M+H)+.

Aufarbeitung

  1. washwashed (1×50 mL) with 5% citric acid
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d7672090db904b5f9d4ad306cb6a019c
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901119B2

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