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Lithium hydroxide, monohydrate → 4-{(S)-5-(6-Bromo-2-methoxy-naphthalen-1-ylmethyl)-3-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carbonyl}-benzoic acid

HRID 1481909
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1481909
C[O:2][C:3](=[O:52])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:18][C@H:17]([NH:19][C:20](=[O:32])[C@@H:21]([N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:24])[CH3:22])[C:16](=[O:33])[N:15]([CH2:34][C:35]3[C:44]4[C:39](=[CH:40][C:41]([Br:45])=[CH:42][CH:43]=4)[CH:38]=[CH:37][C:36]=3[O:46][CH3:47])[C:14]3[CH:48]=[CH:49][CH:50]=[CH:51][C:13]2=3)=[O:11])=[CH:6][CH:5]=1.O[Li].O>C1COCC1.CO.O.O>[Br:45][C:41]1[CH:40]=[C:39]2[C:44](=[CH:43][CH:42]=1)[C:35]([CH2:34][N:15]1[C:16](=[O:33])[C@@H:17]([NH:19][C:20](=[O:32])[C@@H:21]([N:23]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH3:24])[CH3:22])[CH2:18][N:12]([C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:52])=[O:2])=[CH:5][CH:6]=3)=[O:11])[C:13]3[CH:51]=[CH:50][CH:49]=[CH:48][C:14]1=3)=[C:36]([O:46][CH3:47])[CH:37]=[CH:38]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 902212384-{(S)-5-(6-Bromo-2-methoxy-naphthalen-1-ylmethyl)-3-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carbonyl}-benzoic acid methyl ester2×

Produkt 1

HCID 902209134-{(S)-5-(6-Bromo-2-methoxy-naphthalen-1-ylmethyl)-3-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carbonyl}-benzoic acidAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

To a solution of 4-{(S)-5-(6-bromo-2-methoxy-naphthalen-1-ylmethyl)-3-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carbonyl}-benzoic acid methyl ester (Intermediate 19) (4 g, 5.175 mmol) in THF-MeOH-water 1:1:1 (90 mL) were slowly added a solution of LiOH.H2O solution (574 mg, 13.6 m mol) in water. After 4 h the mixture was concentrated, the residue was diluted with water and acidified to pH˜3 with 1 N HCl. The mixture was extracted with ethyl acetate, the extracts were dried over sodium sulfate and evaporated. The residue was triturated with hexane to give the title compound (3.6 g, 91.58%) as an off white solid. LC-MS: 759 (M+H).

Aufarbeitung

  1. concentrationAfter 4 h the mixture was concentrated
  2. additionthe residue was diluted with water
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe extracts were dried over sodium sulfate
  5. customevaporated
  6. customThe residue was triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-5501cc82b23e4b0db6bbdfa3b7077300
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09409888B2

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