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Hydrochloric Acid → 2-{[(1,1-dimethylethyl)oxy]carbonyl}-6-{N-[(methyloxy)carbonyl]-L-valyl}-2,6-diazaspiro[3,4]octane-7-carboxylic acid

HRID 454439
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 454439
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10]([N:12]1[CH:26]([C:27]([O:29]CC)=[O:28])[CH2:25][C:14]2([CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]2)[CH2:13]1)=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4].O.[OH-].[Li+].Cl>C1COCC1.O.CO>[CH3:24][C:21]([O:20][C:18]([N:16]1[CH2:15][C:14]2([CH2:25][CH:26]([C:27]([OH:29])=[O:28])[N:12]([C:10](=[O:11])[C@H:6]([CH:7]([CH3:8])[CH3:9])[NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:13]2)[CH2:17]1)=[O:19])([CH3:22])[CH3:23]
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Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 583130532-(1,1-dimethylethyl) 7-ethyl 6-{N-[(methyloxy)carbonyl]-L-valyl}-2,6-diazaspiro[3,4]octane-2,7-dicarboxylate

Produkt 1

HCID 583130782-{[(1,1-dimethylethyl)oxy]carbonyl}-6-{N-[(methyloxy)carbonyl]-L-valyl}-2,6-diazaspiro[3,4]octane-7-carboxylic acidAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

To a solution of 2-(1,1-dimethylethyl) 7-ethyl 6-{N-[(methyloxy)carbonyl]-L-valyl}-2,6-diazaspiro[3.4]octane-2,7-dicarboxylate (146) (344 mg, 0.78 mmol) in THF/water/methanol (3 mL/1.5 mL/1.5 mL) was added lithium hydroxide monohydrate (65 mg, 1.56 mmol) and the reaction stirred at room temperature for 1.5 h whereupon it was treated with 1N HCl (1.5 mL). The reaction was partitioned between EtOAc and water (30 mL each), the aqueous layer was extracted with EtOAc (30 mL), the organic layers were combined and dried (MgSO4) and concentrated in vacuo to afford the title compound as a white solid (245 mg, 76% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.46 (br. s., 1H) 7.06-7.66 (m, 1H) 4.13-4.32 (m, 1H) 3.88-4.12 (m, 2H) 3.56-3.89 (m, 5H) 3.39-3.57 (m, 3H) 2.24-2.45 (m, 1H) 1.99-2.19 (m, 1H) 1.80-1.95 (m, 1H) 1.26-1.44 (m, 9H) 0.56-1.00 (m, 6H). LC-MS ESI (M−H)−=412.41.

Aufarbeitung

  1. customThe reaction was partitioned between EtOAc and water (30 mL each)
  2. extractionthe aqueous layer was extracted with EtOAc (30 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0a63733e03cd4309afbde14ab8bbdc7c
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492554B2

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