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Lithium hydroxide, monohydrate → 2-(S)-[2-(S)-Allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester

HRID 1595142
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1595142
Cl.C[O:3][C:4](=[O:36])[C@@H:5]([NH:15][C:16](=[O:35])[C@@H:17]([NH:28][C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[NH:27])[NH2:26])=[CH:21][CH:20]=1)[CH2:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].O.[OH-].[Li+]>O.C1COCC1>[C:11]([O:10][C:8](=[O:9])[CH2:7][CH2:6][C@H:5]([NH:15][C:16](=[O:35])[C@@H:17]([NH:28][C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25](=[NH:26])[NH2:27])=[CH:23][CH:24]=1)[C:4]([OH:36])=[O:3])([CH3:14])([CH3:12])[CH3:13]
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Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 686148872-(S)-[2-(S)-Allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride

Produkt 1

HCID 114429402-(S)-[2-(S)-Allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 2-(S)-[2-(S)-allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride (3.06 g, 5.8 mmol) in 100 ml of water and 30 ml of THF was added lithium hydroxide hydrate (0.49 g, 11.6 mmol). The solution was stirred at room temperature for 12 hours, evaporated, and freeze-dried. The residue was purified by chromatography on Sephadex LH20 employing n-butanol/glacial acetic acid/water (17/1/2) as eluent. Pure fractions were combined. The solvent was evaporated, the residue was taken up in water, and the aqueous solution was freeze-dried. Yield: 2.7 g (97%). MS: m/z=477.4 (M+H)+.

Aufarbeitung

  1. customevaporated
  2. customfreeze-dried
  3. customThe residue was purified by chromatography on Sephadex
  4. customThe solvent was evaporated
  5. customthe aqueous solution was freeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-58ac813d6675430ba77c3bc1b1faaa7e
Quelldatensatz
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06287794B1

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