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Hydrochloric Acid → Diphenylmethyl [4-[3-(4-cyanobenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]acetate

HRID 1417218
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1417218
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]([O:15][CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C:8](=[O:29])[C:7]1=[O:30].[C:31]([C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1)#[N:32].C(N(CC)CC)C.Cl>O1CCCC1.O.C(OCC)(=O)C>[C:31]([C:33]1[CH:34]=[CH:35][C:36]([S:39]([NH:2][CH2:3][CH2:4][CH2:5][N:6]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]([O:15][CH:16]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:14])[C:8](=[O:29])[C:7]2=[O:30])(=[O:41])=[O:40])=[CH:37][CH:38]=1)#[N:32]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 67554632Diphenylmethyl [4-(3-aminopropyl)-2,3-dioxopiperazin-1-yl]acetate hydrochloride

Produkt 1

HCID 54344221Diphenylmethyl [4-[3-(4-cyanobenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]acetateAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In 7 ml of tetrahydrofuran was dissolved 0.70 g of diphenylmethyl [4-(3-aminopropyl)-2,3-dioxopiperazin-1-yl]acetate hydrochloride, and 0.36 g of 4-cyanobenzenesulfonyl chloride and then 0.58 ml of triethylamine were added thereto under ice-cooling. After stirring at room temperature for 30 minutes, the reaction mixture was added to a mixed solvent of 20 ml of ethyl acetate and 20 ml of water and the pH was adjusted to 3 with 2N hydrochloric acid. The organic layer was separated, washed with water and then a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; chloroform : methanol=20:1) to obtain 0.43 g of diphenylmethyl [4-[3-(4-cyanobenzenesulfonyl-amino)propyl]-2,3-dioxopiperazin-1-yl]acetate as a yellow foamy substance.

Aufarbeitung

  1. temperatureunder ice-cooling
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent; chloroform : methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-34348df543c44b038955a91700120061
Quelldatensatz
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05877174

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