Ethyl Acetate → 2-{[(Benzyloxy)carbonyl]amino}-3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)-2-propenoic acid methyl ester

HRID 1296218

Reaktionsgleichung

Reaktionsgleichung von HRID 1296218
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:18][CH3:19])=[C:7]([CH:17]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=O.[CH2:20]([O:27][C:28]([NH:30][CH:31](P(OC)(OC)=O)[C:32]([O-:34])=[O:33])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:41]1CCN2C(=NCCC2)CC1.C(OCC)(=O)C>ClCCl>[CH3:41][O:34][C:32](=[O:33])[C:31]([NH:30][C:28]([O:27][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:29])=[CH:1][C:3]1[CH:4]=[CH:5][C:6]([O:18][CH3:19])=[C:7]([CH2:8][NH:9][C:10]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:16])[CH:17]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22493931Tert-butyl (5-formyl-2-methoxybenzyl)carbamateHCID 131726531[(Benzyloxy)carbonyl]amino-2-(dimethoxyphosphoryl)acetate

Produkt 1

HCID 694858062-{[(Benzyloxy)carbonyl]amino}-3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)-2-propenoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.65 g of t-butyl N-(5-formyl-2-methoxybenzyl)carbamate, 3.81 g of methyl 2-([(benzyloxy)carbonyl]amino-2-(dimethoxyphosphoryl)acetate and 1.75 g of 1,8-diazabicyclo[5,4,0]-7-undecene were dissolved in 50 ml of dichloromethane, followed by stirring for 15 hours at room temperature. 300 ml of ethyl acetate was added, and the organic layer was successively washed with 150 ml of water and 150 ml of brine, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography, and 4.09 g of 2-{[(benzyloxy)carbonyl]amino}-3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)-2-propenoic acid methyl ester was obtained as a colorless solid.

Aufarbeitung

  1. washthe organic layer was successively washed with 150 ml of water and 150 ml of brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0477333a245b4dbf88326acc3540545d
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244861B2

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