Triethylamine → 4-acetylamino-5-chloro-2-methoxy-N-[(2S,4S)-1-acetyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide

HRID 1723904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723904
[C:1]([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[C:30]([N:33]1[CH2:37][C@@H:36]([NH2:38])[CH2:35][C@H:34]1[CH2:39][OH:40])(=[O:32])[CH3:31]>ClCCl.O>[C:1]([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9]([NH:38][C@@H:36]2[CH2:37][N:33]([C:30](=[O:32])[CH3:31])[C@H:34]([CH2:39][OH:40])[CH2:35]2)=[O:11])=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 109884964-Acetamido-5-chloro-2-methoxybenzoic acidHCID 450861111-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)ethanone

Produkt 1

HCID 117406984-acetylamino-5-chloro-2-methoxy-N-[(2S,4S)-1-acetyl-2-hydroxymethyl-4-pyrrolidinyl]benzamideAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

9.84 g of 4-acetylamino-5-chloro-2-methoxybenzoic acid, and 4.5 g of triethylamine were dissolved in 40 ml of dichloromethane, and 4.60 g of ethyl chlorocarbonate was added dropwise to the solution at not higher than 10° C. After stirring at the same temperature for 30 minutes, a solution of 7.03 g of (2S,4S)-(−)-1-acetyl-4-amino-2-hydroxymethylpyrrolidine in dichloromethane (20 ml) was added dropwise. After stirring at the same temperature overnight, water (20 ml) was added, precipitated crystals were filtered, and the resulting crystals were dried in a warm air at 50 to 55° C. to obtain 11.74 g of 4-acetylamino-5-chloro-2-methoxy-N-[(2S,4S)-1-acetyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide.

Aufarbeitung

  1. additionwas added
  2. customprecipitated crystals
  3. filtrationwere filtered
  4. customthe resulting crystals were dried in a warm air at 50 to 55° C.

Quellen und Nachweise

ORD-Eintrag
ord-a6d4b715b88c4437a32da0ff07774102
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485665B2

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