4-Methylmorpholine → N-Boc-S-(cyanomethyl)-L-cysteine-L-proline-O-benzyl ester

HRID 1490128

Reaktionsgleichung

Reaktionsgleichung von HRID 1490128
[C:1]([NH:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][S:11][CH2:12][C:13]#[N:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.C([O:26][C:27](=[O:33])[C@@H:28]1[CH2:32][CH2:31][CH2:30][NH:29]1)C1C=CC=CC=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2N=N1.[CH3:61]N1CCOCC1>C(#N)C.C(OCC)(=O)C.CN(C=O)C>[N:29]1([CH:61]([O:16][C:15](=[O:17])[C@H:9]([CH2:10][S:11][CH2:12][C:13]#[N:14])[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:30][CH2:31][CH2:32][C@H:28]1[C:27]([OH:26])=[O:33]

Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2733413Proline benzyl ester hydrochlorideHCID 22874698(R)-2-((tert-butoxycarbonyl)amino)-3-((cyanomethyl)thio)propanoic acid

Produkt 1

HCID 131720088N-Boc-S-(cyanomethyl)-L-cysteine-L-proline-O-benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The compound of Example 71 (24.72, 95.06 mmole) and L-proline-O-benzyl ester hydrochloride (22.98 g, 95.06 mmole) are suspended in 140 mL of acetonitrile and 120 mL of DMF at 0° C., then BOP (42.0 g, 95.06 mmole) and NMM (28.84 g, 285.18 mmole) are added. The ice bath is removed after 30 minutes and the reaction is stirred for 18 hours at room temperature. The reaction mixture is reduced in volume under vacuum at 25° C. to give a residue. The residue is taken up in 200 mL ethyl acetate, and is washed successively with 1N hydrochloric acid (1×50 mL) saturated sodium bicarbonate 1×50 mL) and brine (1×50 mL). After drying with MgSO4, the solvent is evaporated under vacuum to give the title compound.

Aufarbeitung

  1. customThe ice bath is removed after 30 minutes
  2. customis reduced in volume under vacuum at 25° C.
  3. customto give a residue
  4. washis washed successively with 1N hydrochloric acid (1×50 mL) saturated sodium bicarbonate 1×50 mL) and brine (1×50 mL)
  5. dry with materialAfter drying with MgSO4
  6. customthe solvent is evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1db4c1b9528b406fa92544970b4a7b98
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05681844

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