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Triethylamine → HCID 22821052, Verbindung

HRID 1980046
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1980046
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15](O)=[O:16])[C:10](=[O:18])[CH:9]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:22][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.C(OC(Cl)=O)C(C)C.Cl.[NH2:50][CH2:51][C:52]([NH:54][C@H:55]([C:63]([NH:65][CH3:66])=[O:64])[CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:53]>O.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:50][CH2:51][C:52]([NH:54][C@H:55]([C:63]([NH:65][CH3:66])=[O:64])[CH2:56][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)=[O:53])=[O:16])[C:10](=[O:18])[CH:9]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:22][CH:21]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 20437871HCID 20437871, VerbindungHCID 22821046HCID 22821046, Verbindung

Produkt 1

HCID 22821052HCID 22821052, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a solution of piperazinone acetic acid 5a (0.45 g, 1.0×10-3 mole) and dry THF (3 ml) at -10° C. under argon is added in turn Et3N (0.16 ml, 1.1×10-3 mole) and isobutylchloroformate (0.15 ml, 1.1×10-3 mole). After stirring 10 minutes at -10° C., a freshly neutralized solution of glycyl-L-phenylalanine methyl amide 9a hydrochloride (0.30 g, 1.1×10-3 mole), Et3N (0.28 ml, 2.0×10-3 mole), THF (3 ml), and H2O (1.5 ml) is added in one portion. The cooling bath is then removed and the reaction allowed to warm to room temperature. After stirring overnight the reaction is quenched into 0.5M aqueous HCl. The aqueous mixture is extracted with Et2O (2 times) and CH2Cl2 (2 times). The ethereal extracts are combined and washed with saturated aqueous NaHCO3 as are the CH2Cl2 extracts. The ethereal and CH 2 Cl2 extracts are then combined and dried over Na2SO4. Filtration of the drying agent and evaporation of the filtrate give 10a which is purified by chromatography, and the structure corroborated by NMR. NMR (CDCl3) δ 1.26 (S, 9, t-boc), 2.64 (d, 3, methylamide), 3.08, 3.90 (m, 12, methylenes), 4.68 (m, 2, C3 -H and phenylala --CH), 4.98 (S, 2, benzyloxy methylene), 6.6-7.8 (m, 17, aromatic and amide NH's).

Aufarbeitung

  1. customThe cooling bath is then removed
  2. temperatureto warm to room temperature
  3. stirringAfter stirring overnight the reaction
  4. customis quenched into 0.5M aqueous HCl
  5. extractionThe aqueous mixture is extracted with Et2O (2 times) and CH2Cl2 (2 times)
  6. washwashed with saturated aqueous NaHCO3
  7. dry with materialdried over Na2SO4
  8. filtrationFiltration of the drying agent and evaporation of the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-ee6b96bf7a5d4f3ba74492cf4e2c963a
Quelldatensatz
uspto-grants-1984_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04483988

Notizen zur Reaktion

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