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Sodium Hydroxide → 4-biphenyl-4-ylmethyl-1-[2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl]-piperidine-4-carboxylic acid

HRID 2360968
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2360968
C[O:2][C:3]([C:5]1([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)[CH2:10][CH2:9][N:8]([C:11](=[O:27])[C@@H:12]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>C1COCC1.CO>[C:32]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[CH:34][C:29]([CH2:28][C:5]2([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][N:8]([C:11](=[O:27])[C@@H:12]([NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:13][C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)[CH2:7][CH2:6]2)=[CH:30][CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 673851184-biphenyl-4-ylmethyl-1-[2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl]-piperidine-4-carboxylic acid methyl ester

Produkt 1

HCID 673846684-biphenyl-4-ylmethyl-1-[2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl]-piperidine-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of 4-biphenyl-4-ylmethyl-1-[2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl]-piperidine-4-carboxylic acid methyl ester (5.63 mmol; 3.17 g) in THF (30 mL) and methanol (20 mL) was added a 1M solution of sodium hydroxide (16.9 mmol; 16.9 mL) and the resulting mixture was heated to reflux for 48 hours. The resulting mixture was then evaporated and a 1N hydrochloric acid solution (200 mL) was added to the residue. A white precipitate formed that was separated via filtration to yield 4-biphenyl-4-ylmethyl-1-[2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl]-piperidine-4-carboxylic acid. MS (ESI) m/z 547.44 [M+H]+.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 48 hours
  3. customThe resulting mixture was then evaporated
  4. additiona 1N hydrochloric acid solution (200 mL) was added to the residue
  5. customA white precipitate formed
  6. customthat was separated via filtration

Quellen und Nachweise

ORD-Eintrag
ord-bd0a050957354836b87182b3ab7d7894
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08686152B2

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