Triethylamine → 3-(4-Benzyloxy-benzoylamino)-propionic acid methyl ester

HRID 1669222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669222
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:19][O:20][C:21](=[O:25])[CH2:22][CH2:23][NH2:24].C(N(CC)CC)C.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:19][O:20][C:21](=[O:25])[CH2:22][CH2:23][NH:24][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 738804-(Benzyloxy)benzoic acidHCID 2734767Methyl 3-aminopropanoate hydrochloride

Produkt 1

HCID 266353683-(4-Benzyloxy-benzoylamino)-propionic acid methyl esterAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of 4-benzyloxybenzoic acid (8.92 g, 39.08 mmol) and 3-amino-propionic acid methyl ester hydrochloride (6.00 g, 42.98 mmol) in CH2Cl2 (100 mL) was added DMAP (catalytic), triethylamine (6.60 mL, 47.35 mmol), and EDCI (9.00 g, 46.94 mmol). The mixture was stirred at RT for 12 h. The mixture was diluted with CH2Cl2. The organics were washed with 1N HCl, 2N NaOH, water, and brine (1×100 mL each), and dried with MgSO4 to yield 11.28 g (92%) of the title compound.

Aufarbeitung

  1. washThe organics were washed with 1N HCl, 2N NaOH, water, and brine (1×100 mL each)
  2. dry with materialdried with MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-74926c26f41f46d1b5bfbc364f15b45c
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989457B2

Notizen zur Reaktion

Wird geladen…