(Z)-1-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-3-methoxy-3-oxoprop-1-en-2-yl benzoate → (R)-3-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate

HRID 132439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132439
[C:1]([O:9]/[C:10](/[C:32]([O:34][CH3:35])=[O:33])=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:14]([CH3:26])[C:13]=1[CH2:27][O:28][C:29](=[O:31])[CH3:30])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>ClCCl.[B-](F)(F)(F)F.CC[C@H]1P(C2C(P3[C@H](CC)CC[C@H]3CC)=CC=CC=2)[C@H](CC)CC1.C1[CH][CH]CC[CH][CH]C1.[Rh]>[C:1]([O:9][C@H:10]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])=[C:14]([CH3:26])[C:13]=1[CH2:27][O:28][C:29](=[O:31])[CH3:30])[C:32]([O:34][CH3:35])=[O:33])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 59732069(Z)-1-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-3-methoxy-3-oxoprop-1-en-2-yl benzoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 59732072(R)-3-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11549211CID 11549211KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(Z)-1-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-3-methoxy-3-oxoprop-1-en-2-yl benzoate (20.00 g, 41.4 mmol) in dichloromethane (120.00 ml) was added (−)-1,2-bis((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I)tetrafluoroborate (280.00 mg, 0.424 mmol) under nitrogen atmosphere. The reaction mixture was hydrogenated at 60 psi pressure of hydrogen for 12h. The solvent was removed and crude product was carried to the next step as such. MS (ESI) 508 (M+H); Rf=2.53.

Aufarbeitung

  1. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-8fa164879af04b39828fbffe1f1ae5f7
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384931B2

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