Acetic Anhydride → acetic acid (S)-4-[3-(4-chloro-phenoxy)-azetidin-1-yl]-2-[3-(3,5-dimethoxy-phenyl)-ureido]-butyl ester

HRID 1182138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182138
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][CH:7]2[CH2:10][N:9]([CH2:11][CH2:12][C@H:13]([NH:16][C:17]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[CH:21]=3)=[O:18])[CH2:14][OH:15])[CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:39](OC(=O)C)(=[O:41])[CH3:40]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH2:8][N:9]([CH2:11][CH2:12][C@H:13]([NH:16][C:17]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[CH:21]=3)=[O:18])[CH2:14][O:15][C:39](=[O:41])[CH3:40])[CH2:10]2)=[CH:30][CH:31]=1

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 102384451-[(S)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl)-3-(3,5-dimethoxy-phenyl)-urea

Produkt 1

HCID 10128172acetic acid (S)-4-[3-(4-chloro-phenoxy)-azetidin-1-yl]-2-[3-(3,5-dimethoxy-phenyl)-ureido]-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-{(S)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3-(3,5-dimethoxy-phenyl)-urea (0.05 g, 0.111 mmol) and triethylamine (0.031 ml, 0.222 mmol) in DCM (3 ml) is treated with acetic anhydride and left to stir at room temperature for 3 hours. The reaction mixture is partitioned between DCM and water. The organic phase is washed with sodium bicarbonate solution, dried over magnesium sulphate and evaporated to afford acetic acid (S)-4-[3-(4-chloro-phenoxy)-azetidin-1-yl]-2-[3-(3,5-dimethoxy-phenyl)-ureido]-butyl ester. [M+H] 492.08

Aufarbeitung

  1. waitleft
  2. customThe reaction mixture is partitioned between DCM and water
  3. washThe organic phase is washed with sodium bicarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3c9ec38c96e1442eb84456a66a9eb8b3
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288537B2

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