Sodium Bicarbonate → Methyl 3-{2-[(acetyloxy)methyl]-4-[(tert-butoxycarbonyl)amino]-3-methylphenyl}-2-{[(benzyloxy)carbonyl]amino}prop-2-enoate

HRID 132289

Reaktionsgleichung

Reaktionsgleichung von HRID 132289
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([CH3:21])=[C:11]([C:17](I)=[CH:18][CH:19]=1)[CH2:12][O:13][C:14](=[O:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][O:23][C:24]([C:26]([NH:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[CH2:27])=[O:25].C(=O)(O)[O-].[Na+]>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:22][O:23][C:24](=[O:25])[C:26]([NH:28][C:29]([O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:30])=[CH:27][C:17]1[CH:18]=[CH:19][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:10]([CH3:21])[C:11]=1[CH2:12][O:13][C:14](=[O:16])[CH3:15]

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 3525700Z-Dehydro-Ala-OMeHCID 534147073-(Tert-butoxycarbonylamino)-6-iodo-2-methylbenzyl acetate

Produkt 1

HCID 53415138Methyl 3-{2-[(acetyloxy)methyl]-4-[(tert-butoxycarbonyl)amino]-3-methylphenyl}-2-{[(benzyloxy)carbonyl]amino}prop-2-enoateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 16212273Tetrabutylammonium chloride hydrateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Palladium (II) acetate (105 mg, 0.43 mmol) was added to a mixture of acetic acid 3-tert-butoxycarbonylamino-6-iodo-2-methyl-benzyl ester (2.89 g, 7.1 mmol), Z-dehydroalanine methyl ester (2.20 g, 9.4 mmol), tetrabutylammonium chloride hydrate (2.70 g, 9.7 mmol), and sodium bicarbonate (1.80 g, 21.4 mmol) in THF (100 mL). Reaction was heated at reflux for 3.75 hours. Mixture was cooled to room temperature then filtered through a plug of silica gel eluting 70% ethyl acetate-hexanes (500 mL). Filtrate was concentrated in vacuo. Silica gel chromatography afforded the title compound as a yellow solid in 69% yield. 1H NMR (300 MHz, CDCl3): δ=7.79 (d, J=8.4, 1H), 7.42 (s, 1H), 7.27 (m, 6H), 6.30 (s, 1H), 5.11 (s, 2H), 5.02 (s, 2H), 3.81 (s, 3H), 2.21 (s, 3H), 2.02 (s, 3H), 1.51 (s, 9H). MS m/e (M−H)−=511.0.

Aufarbeitung

  1. customReaction
  2. temperaturewas heated
  3. temperatureat reflux for 3.75 hours
  4. filtrationthen filtered through a plug of silica gel eluting 70% ethyl acetate-hexanes (500 mL)
  5. concentrationFiltrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-439f2396daaf45e8a85daf34b08fefa2
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384931B2

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