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tert-butyl 3-({3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate → tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

HRID 548769
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 548769
[CH3:1][C@H:2]([O:6][C:7]1[CH:8]=[C:9]([C:21]([NH:23][C:24]2[CH:28]=[CH:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[N:25]=2)=[O:22])[CH:10]=[C:11]([O:13]CC2C=CC=CC=2)[CH:12]=1)[CH2:3][O:4][CH3:5]>C1COCC1.C(O)C>[OH:13][C:11]1[CH:10]=[C:9]([C:21]([NH:23][C:24]2[CH:28]=[CH:27][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[N:25]=2)=[O:22])[CH:8]=[C:7]([O:6][C@@H:2]([CH3:1])[CH2:3][O:4][CH3:5])[CH:12]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 59127136tert-butyl 3-({3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

Produkt 1

HCID 59127185tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylateAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1,1-dimethylethyl 3-[({3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(phenylmethyl)oxy]phenyl}carbonyl)amino]-1H-pyrazole-1-carboxylate (23 g, 47.8 mmol) in THF (140 mL) and ethanol (140 mL) was evacuated and purged with nitrogen (×3). 10% Palladium on carbon (2.3 g; 10% w/w) was added and reaction mixture was evacuated and finally purged with hydrogen gas. The reaction mixture was left to stir at RT under a hydrogen balloon for 16 hours. The palladium on carbon was filtered through diatomaceous earth and the filtrate concentrated in vacuo to give a white foam (18 g).

Aufarbeitung

  1. custompurged with nitrogen (×3)
  2. addition10% Palladium on carbon (2.3 g; 10% w/w) was added
  3. customreaction mixture
  4. customwas evacuated
  5. customfinally purged with hydrogen gas
  6. waitThe reaction mixture was left
  7. filtrationThe palladium on carbon was filtered through diatomaceous earth
  8. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4c1f2a21940747c4b94dcafe9ea99558
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07943607B2

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