Water → (2S)-cyclopentyl[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)amino]ethanoic acid

HRID 522362

Reaktionsgleichung

Reaktionsgleichung von HRID 522362
[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[O:9][C:10]([O:12]N1C(=O)CCC1=O)=O)[CH2:2][CH2:3][C:4]#[CH:5].[NH2:20][C@@H:21]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27]C1)[C:22]([OH:24])=[O:23].C(N(CC)CC)C.O>C(#N)C.C(OCC)(=O)C>[CH:25]1([C@H:21]([NH:20][C:10]([O:9][C@@H:7]2[CH2:8][C@H:6]2[CH2:1][CH2:2][CH2:3][C:4]#[CH:5])=[O:12])[C:22]([OH:24])=[O:23])[CH2:30][CH2:29][CH2:28][CH2:27]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 736848(alphaS)-alpha-Aminocyclohexaneacetic acidHCID 895908351-[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)oxy]pyrrolidine-2,5-dione

Produkt 1

HCID 89590843(2S)-cyclopentyl[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)amino]ethanoic acidAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the product of Step 1 (457 mg) in acetonitrile (6 ml) was added (2S)-amino(cyclohexyl)ethanoic acid (352 mg) followed by triethylamine (0.720 ml) and water (6.00 ml). The mixture was stirred at room temperature for 18 hours. The mixture was diluted with ethyl acetate and washed with HCl 1N, water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. This provided the desired product (510 mg) as an oil. LRMS (ES+) M/Z (M+H)+ 308.2.

Aufarbeitung

  1. washwashed with HCl 1N, water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fac0f28567ba41b0ab7b91c86f3a0bfb
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328138B2

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