2-Methylmorpholine → 6-Chloro-N-{(3S)-1-[(1S)-1-methyl-2-(2-methylmorpholin-4-yl)-2-oxoethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamide

HRID 2110067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110067
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C@@H:21]([CH3:25])[C:22]([OH:24])=O)[C:17]1=[O:26])(=[O:14])=[O:13])[CH:6]=[CH:5]2.[CH3:27][CH:28]1[O:33][CH2:32][CH2:31][NH:30][CH2:29]1>C(Cl)Cl.CN(C=O)C.C(N(CC)C(C)C)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C@@H:21]([CH3:25])[C:22]([N:30]3[CH2:31][CH2:32][O:33][CH:28]([CH3:27])[CH2:29]3)=[O:24])[C:17]1=[O:26])(=[O:13])=[O:14])[CH:6]=[CH:5]2

Komponenten

6

Edukt 2

HCID 4106152-MethylmorpholineHCID 69058818(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid

Produkt 1

HCID 690663266-Chloro-N-{(3S)-1-[(1S)-1-methyl-2-(2-methylmorpholin-4-yl)-2-oxoethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamideAusbeute 44,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

To polymer N-cyclohexylcarbodiimide-N′-propyloxymethyl polystyrene (0.038 g) in an Alltech™ tube was added a solution of (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid (0.007 g) in DCM (0.9 ml) followed by 2-methylmorpholine (0.004 g) in DMF (0.1 ml) and N,N-diisopropylethylamine (0.006 ml). The mixture was shaken at room temperature for 4 days. The tube was drained, the filtrate collected and the resin washed with DCM. The combined DCM solutions were concentrated under reduced pressure and the residue purified by mass directed preparative h.p.l.c. to give the title compound (0.0038 g) as an off-white solid.

Aufarbeitung

  1. customthe filtrate collected
  2. washthe resin washed with DCM
  3. concentrationThe combined DCM solutions were concentrated under reduced pressure
  4. customthe residue purified by mass

Quellen und Nachweise

ORD-Eintrag
ord-d337c7b7734a42b992d187be034be851
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517879B2

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