4-Methylmorpholine → HCID 66843294, Verbindung

HRID 254044

Reaktionsgleichung

Reaktionsgleichung von HRID 254044
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:33](=[O:34])[C@H:32]([S:35][CH2:36][C:37]([C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=3)=[O:38])[C@H:31]2[C:46]2[CH:60]=[CH:59][C:49]([O:50][CH2:51][C:52]([NH:54][CH2:55][C:56](O)=[O:57])=[O:53])=[CH:48][CH:47]=2)=[CH:26][CH:25]=1.CN1CCOCC1.[NH2:68][C@@H:69]([C:74]([OH:76])=[O:75])[C:70]([CH3:73])([CH3:72])[CH3:71].[BH4-].[Na+]>C(Cl)Cl.CO>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]2[C:33](=[O:34])[C@H:32]([S:35][CH2:36][CH:37]([C:39]3[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=3)[OH:38])[C@H:31]2[C:46]2[CH:47]=[CH:48][C:49]([O:50][CH2:51][C:52]([NH:54][CH2:55][C:56]([NH:68][C@@H:69]([C:74]([OH:76])=[O:75])[C:70]([CH3:73])([CH3:72])[CH3:71])=[O:57])=[O:53])=[CH:59][CH:60]=2)=[CH:28][CH:29]=1

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 4311764Sodium borohydrideHCID 6950340D-tert-leucineHCID 66842755HCID 66842755, Verbindung

Produkt 1

HCID 66843294HCID 66843294, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TBTU (0.020 g, 0.063 mmol) was added to a solution of N-{[4-((2R,3R)-1-(4-chlorophenyl)-3-{[2-(4-chlorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycine (0.030 g, 0.052 mmol) and N-methylmorpholine (0.016 g, 0.157 mmol) in CH2Cl2 (5 ml) at 30° C. After 30 minutes, D-tert-leucine (0.008 g, 0.063 mmol) was added and the mixture was stirred for 30 minutes. The reaction mixture was concentrated. Toluene (2 ml) was added and evaporated. MeOH (3 ml) and sodium borohydride (0.020 g, 0.523 mmol) were added. Full conversion to the corresponding alcohol was obtained after 5 minutes. The reaction was quenched by the addition of 0.1M NH4OAc (1 ml) buffer and the mixture was concentrated. The residue was purified by preparative HPLC using an eluent of 0-50% CH3CN in 0.1M NH4OAc buffer. Freeze-drying of the pure fractions afforded the title compound (0.021 g, 58%) as a colourless solid. 1H NMR [(CD3)2SO), 400 MHz] δ0.85 (s, 9H), 2.82-2.98 (m, 2H), 3.75-3.81 (m, 2H), 3.91-3.96 (m, 1H), 4.29-4.37 (m, 1H), 4.52 (s, 2H), 4.70-4.78 (m, 1H), 5.01-5.06 (m, 1H), 6.97-6.99 (m, 2H), 7.19-7.21 (m, 2H), 7.32-7.36 (m, 8H), 7.52-7.63 (m, 1H), 8.27-8.32 (m, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionToluene (2 ml) was added
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ed6a81a2cdfe4f71a984819335e22d5f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07871998B2

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