Diethyl Ether → 2-[(1-Methoxymethoxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester

HRID 238897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238897
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][C:6]=1[C:15]([OH:17])=O.Cl.[CH3:19][O:20][C:21](=[O:26])[C:22]([NH2:25])([CH3:24])[CH3:23].C(N(CC)C(C)C)(C)C.C(OCC)C>CN(C)C=O.O>[CH3:19][O:20][C:21](=[O:26])[C:22]([NH:25][C:15]([C:6]1[CH:7]=[CH:8][C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[C:5]=1[O:4][CH2:3][O:2][CH3:1])=[O:17])([CH3:24])[CH3:23]

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 688443591-Methoxymethoxy-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid

Produkt 1

HCID 688409232-[(1-Methoxymethoxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl esterAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a round bottom flask was placed 0.96 g 1-methoxymethoxy-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid, 1.25 g 2-amino-2-methyl-propionic acid methyl ester hydrochloride, 3.09 g of O-(7-azabenzotriazole-1-yl)-N,N,N,N-tetramethyluronium hexafluoro phosphate and 2.83 ml of N,N-diisopropylethylamine in 60 ml of N,N-di-methylformamide. It was left stirring at room temperature overnight. 60 ml of diethylether and 60 ml of water were added to the reaction. The organic layer was separated and washed again with 50 ml of water. It was dried over magnesium sulphate, filtered and concentrated in vacuo to afford a crude yellow oil. Purification was performed by flash chromatography (silica, heptanes/ethyl acetate) to give 1.04 g 2-[(1-methoxymethoxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester.

Aufarbeitung

  1. customIn a round bottom flask was placed
  2. waitIt was left
  3. customThe organic layer was separated
  4. washwashed again with 50 ml of water
  5. dry with materialIt was dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a crude yellow oil
  9. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-db2a7331d0d94b898a20155a54c3122b
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642643B2

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