Triphenylphosphine → tert-butyl (R)-2-(3-benzyloxycarbonylamino-6-bromo-2-tert-butoxycarbonylphenoxymethyl)-azetidine-1-carboxylate

HRID 715980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 715980
N(C([O-])=O)=NC([O-])=O.[CH2:9]([O:16][C:17]([NH:19][C:20]1[C:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[C:24]([OH:33])[C:23]([Br:34])=[CH:22][CH:21]=1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O[CH2:36][C@H:37]1[CH2:40][CH2:39][N:38]1[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:9]([O:16][C:17]([NH:19][C:20]1[C:25]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[C:24]([C:23]([Br:34])=[CH:22][CH:21]=1)[O:33][CH2:36][C@H:37]1[CH2:40][CH2:39][N:38]1[C:41]([O:43][C:44]([CH3:45])([CH3:47])[CH3:46])=[O:42])=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 11074142(R)-1-Boc-2-azetidinemethanolHCID 51573101N-carboxylatoiminocarbamateHCID 70982946Tert-butyl 6-benzyloxycarbonylamino-3-bromo-2-hydroxybenzoate2×

Produkt 1

HCID 71003751tert-butyl (R)-2-(3-benzyloxycarbonylamino-6-bromo-2-tert-butoxycarbonylphenoxymethyl)-azetidine-1-carboxylateAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Disopropyl azodicarboxylate (0.717 g) was added to a solution of tert-butyl 6-benzyloxycarbonylamino-3-bromo-2-hydroxybenzoate (Intermediate 48, 1.25 g), tert-butyl (R)-2-hydroxymethylazetidine-1-carboxylate (0.665 g) and triphenylphosphine (0.93 g) in anhydrous THF (20 mL) and the resultant mixture was stirred at room temperature for 30 minutes. The solution was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20% to give tert-butyl (R)-2-(3-benzyloxycarbonylamino-6-bromo-2-tert-butoxycarbonylphenoxymethyl)-azetidine-1-carboxylate (1.74 g) as a colourless gum.

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was purified by chromatography on silica
  3. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20%

Quellen und Nachweise

ORD-Eintrag
ord-ab2538d19e424ebd8bcc87d3be46b5c7
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187494B2

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