Methanol → Methyl cis(+/-)-2-(acetylamino)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate

HRID 43805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43805
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C@H:15]([NH:18][C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[C@H:14]([O:29][CH3:30])[CH2:13]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:31](Cl)(=[O:33])[CH3:32].C(N(CC)CC)C.CO>C(Cl)Cl>[C:31]([NH:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C@H:15]([NH:18][C:19]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:20])[C@H:14]([O:29][CH3:30])[CH2:13]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])(=[O:33])[CH3:32]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86648749Methyl cis(+/-)-2-amino-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate

Produkt 1

HCID 86648750Methyl cis(+/-)-2-(acetylamino)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl cis(±)-2-amino-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate obtained in Example (185b) (300 mg) was dissolved in methylene chloride (25 ml). Acetyl chloride (0.1 ml) and triethylamine (0.2 ml) were added, and the mixture was stirred at room temperature for one hour. Methanol was added to the reaction solution, followed by concentration under reduced pressure. Then, the residue was diluted with ethyl acetate, washed with water, and then concentrated under reduced pressure to obtain the title compound. The resulting compound was used for the next reaction without purification.

Aufarbeitung

  1. concentrationfollowed by concentration under reduced pressure
  2. additionThen, the residue was diluted with ethyl acetate
  3. washwashed with water
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-301e85e79ab048d3a4a677f624879237
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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