N-(Triphenylmethyl)-L-asparagine → Z-Ala-Ala-Asn(Trt)-OH

HRID 1180362

Reaktionsgleichung

Reaktionsgleichung von HRID 1180362
[NH2:1][C@H:2]([C:26]([OH:28])=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH:29]([C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48])[C@H:30]([C:32]([NH:34][C@H:35]([C:37](ON1C(=O)CCC1=O)=[O:38])[CH3:36])=[O:33])[CH3:31]>CN(C=O)C.C(OCC)(=O)C>[NH:29]([C:47]([O:49][CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)=[O:48])[C@H:30]([C:32]([NH:34][C@H:35]([C:37]([NH:1][C@H:2]([C:26]([OH:28])=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:38])[CH3:36])=[O:33])[CH3:31]

Komponenten

5

Edukt 2

HCID 7408309N-(Triphenylmethyl)-L-asparagineHCID 12876467HCID 12876467, Verbindung

Produkt 1

HCID 131726639Z-Ala-Ala-Asn(Trt)-OH

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The tripeptide Z-Ala-Ala-Asn(Trt)-OH (2) was prepared according to the following procedure: To a stirred solution of H-Asn(Trt)-OH (4.97 g, 13.28 mmol, obtained from Bachem) in dry DMF (25 ml) a solution of Z-Ala-Ala-OSu (5.2 g, 13.28 mmol) in dry DMF (20 ml) was added and stirred for 14 h at room temperature. The solvent was evaporated in vacuo by using an oil pump. The obtained crude compound was dissolved in ethyl acetate (100 ml), washed with 1 N HCl (2×30 ml) and water (30 ml). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the tripeptide as a white solid (7.95 g, 92%) of m.p. 196° C. The peptide was used without further purification.—1H NMR (500 MHz, DMSO-d6): δ=1.18 (d, 3 H, J=7.1 Hz, CH3), 1.22 (d, 3 H, J=7.0 Hz, CH3), 2.62-2.88 (m, 2 H, CHCH2), 4.06-4.12 (m, 1 H, CH), 4.31-4.37 (m, 1 H, CH), 4.46-4.50 (m, 1 H, CH), 4.98-5.04 (m, 2 H, CH2O), 7.15-7.35 (m, 20 H, aryl-H). —MS(EI) m/z (%): 651 [M+H+], 673 [M+Na+], 689 [M+K+].

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customThe obtained crude compound
  3. washwashed with 1 N HCl (2×30 ml) and water (30 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-134571c8d76e4950a5bc60909b0fcffc
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279550B2

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