Toluene → (2R,4S)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine

HRID 1941604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1941604
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].[C:6]([S:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:12]([CH2:22]O)[CH2:11]1)(=[O:8])[CH3:7].C([O:26][C:27](N=NC(OCC)=O)=[O:28])C.[C:36]1([CH3:42])[CH:41]=CC=C[CH:37]=1>O1CCCC1>[C:6]([S:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[C@@H:12]([CH2:22][N:4]([C:27]([O:28][C:36]([CH3:42])([CH3:41])[CH3:37])=[O:26])[S:1](=[O:3])(=[O:2])[NH2:5])[CH2:11]1)(=[O:8])[CH3:7]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 82267SulfamideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57080293tert-Butyl (2R,4S)-4-(acetylsulfanyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 57156698(2R,4S)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Preparation of a sulfamide compound To a solution of (2R,4S)-4-acetylthio-1-t-butoxycarbonylpyrrolidine-2-methanol (i.e., a substrate) in tetrahydrofuran (THF) triphenylphosphine (PPh3) N-t-butoxycarbonylsulfamide (BSMD), and azodicarboxylic acid diethyl ester (DEAD) are successively added under ice cooling. The conditions for this reaction are shown in Table 2, Step A-6. The reaction mixture is diluted with toluene, concentrated, diluted with toluene, and the formed crystals are filtered off. The filtrate is concentrated. The residue is purified by silica gel column chromatography to give (2R,4S)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine.

Aufarbeitung

  1. concentrationconcentrated
  2. additiondiluted with toluene
  3. filtrationthe formed crystals are filtered off
  4. concentrationThe filtrate is concentrated
  5. customThe residue is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5ee6fa901ec94c91b0569f27dfffb32f
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05703243

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