1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl [(2,3-difluorobenzoyl)amino]acetate

HRID 41743

Reaktionsgleichung

Reaktionsgleichung von HRID 41743
[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH3:13][O:14][C:15](=[O:18])[CH2:16][NH2:17].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>O1CCCC1>[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:17][CH2:16][C:15]([O:14][CH3:13])=[O:18])=[O:6]

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 3705902,3-Difluorobenzoic acid

Produkt 1

HCID 59816250Methyl [(2,3-difluorobenzoyl)amino]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2,3-difluorobenzoic acid (0.190 g, 1.2 mmol) in tetrahydrofuran (5 mL) were added glycine methyl ester hydrochloride (0.150 g, 1.2 mmol), HOBt (0.162 g, 1.2 mmol), DIEA (0.209 mL, 1.2 mmol) and EDCI (0.252 g, 1.3 mmol). The reaction mixture was allowed to stir overnight. The reaction mixture was quenched with a saturated solution of sodium bicarbonate and the product partitioned into DCM. Separation of the organic layer followed by removal of the solvent gave methyl [(2,3-difluorobenzoyl)amino]acetate which was used in the next step without purification.

Aufarbeitung

  1. customThe reaction mixture was quenched with a saturated solution of sodium bicarbonate
  2. customthe product partitioned into DCM
  3. customSeparation of the organic layer
  4. customfollowed by removal of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-f37486ab661d4d7e81d226a8461f809e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530694B2

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