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C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine → (R)-1-[2-Hydroxy-3-(2-{[(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-3,4-dioxocyclobut1-enylamino)benzoyl]pyrrolidine-2-carboxylic acid

HRID 1528161
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1528161
[CH3:1][C:2]1[O:6][C:5]([CH:7]([NH2:13])[C:8]2([CH3:12])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.C([O:16][C:17]1[C:20](=[O:21])[C:19](=O)[C:18]=1[NH:23][C:24]1[C:25]([OH:40])=[C:26]([CH:37]=[CH:38][CH:39]=1)[C:27]([N:29]1[CH2:33][CH2:32][CH2:31][C@@H:30]1[C:34]([OH:36])=[O:35])=[O:28])C>CO.C(OCC)C>[OH:40][C:25]1[C:24]([NH:23][C:18]2[C:17](=[O:16])[C:20](=[O:21])[C:19]=2[NH:13][CH:7]([C:5]2[O:6][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:8]2([CH3:12])[CH2:9][O:10][CH2:11]2)=[CH:39][CH:38]=[CH:37][C:26]=1[C:27]([N:29]1[CH2:33][CH2:32][CH2:31][C@@H:30]1[C:34]([OH:36])=[O:35])=[O:28]
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Komponenten

5

Edukt 2

HCID 89525357C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine2×HCID 89534485(R)-1-[3-(2-Ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxybenzoyl]pyrrolidine-2-carboxylic acid

Produkt 1

HCID 71555296(R)-1-[2-Hydroxy-3-(2-{[(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-3,4-dioxocyclobut1-enylamino)benzoyl]pyrrolidine-2-carboxylic acidAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
2×
HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

494 mg (2.73 mmol) of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine in 3 ml of methanol were added to a solution of 500 mg (1.34 mmol) of (R)-1-[3-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-benzoyl]pyrrolidine-2-carboxylic acid in 47 ml of methanol at 50° C. After 3 days, 248 mg (1.37 mmol) of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine were added. After 4 days, the reaction medium was concentrated to dryness. The reaction medium was taken up in ethyl acetate and was washed with a saturated aqueous ammonium chloride solution and then with a 1 M aqueous solution of sodium dihydrogen phosphate. The organic phase was dried over magnesium sulfate, filtered and concentrated. The solid obtained was taken up, with stirring, in diethyl ether and a little ethyl acetate and was filtered. 400 mg of a beige solid were obtained. This solid was chromatographed on silica gel (ethyl acetate/acetone/water: 50/50/2 then 50/50/5). 240 mg were obtained in the form of a beige solid. Yield=35%, HPLC=52.43%+45.15% (mixture of the two diastereoisomers), Mp=198-205° C.

Aufarbeitung

  1. waitAfter 4 days
  2. concentrationthe reaction medium was concentrated to dryness
  3. washwas washed with a saturated aqueous ammonium chloride solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe solid obtained
  8. filtrationa little ethyl acetate and was filtered

Quellen und Nachweise

ORD-Eintrag
ord-c4dd62464bd349e484661227cfd6f189
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090596B2

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