Diisopropylcarbodiimide → Tert-butyl n-(2-tert-butoxy-2-oxoethyl)-n-[(1-oxo-2,3-dihydro-1h-inden-4-yl)carbonyl]glycinate

HRID 2377235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377235
[O:1]=[C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=O)[C:5]=2[CH2:4][CH2:3]1.C(N=C=NC(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.[NH:34]([CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>ClCCl>[C:39]([O:38][C:36](=[O:37])[CH2:35][N:34]([C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][C:2]2=[O:1])=[O:13])[CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])([CH3:42])([CH3:41])[CH3:40]

Komponenten

6

Edukt 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 4393691DI-T-Butyl iminodiacetateHCID 125422061-Oxo-indan-4-carboxylic acid

Produkt 1

HCID 69199393Tert-butyl n-(2-tert-butoxy-2-oxoethyl)-n-[(1-oxo-2,3-dihydro-1h-inden-4-yl)carbonyl]glycinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Example 5 (500 mg, 2.84 mmol) in dichloromethane (10 mL) was added 1,3-diisopropylcarbodiimide (0.44 mL, 2.84 mmol), 1-hydroxybenzotriazole hydrate (115 mg, 0.85 mmol), and di-t-butyl iminodiacetate (1.04 g, 4.26 mmol). The mixture was stirred at room temperature for about 24 hours, quenched with water, and extracted with diethyl ether. The combined organic extracts were washed with brine and saturated aqueous sodium bicarbonate, dried (Na2SO4), filtered and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using hexane/ethyl acetate (1:1) as the mobile phase to provide the desired product. MS (ESI): m/z 402 (M−H)−.

Aufarbeitung

  1. customquenched with water
  2. extractionextracted with diethyl ether
  3. washThe combined organic extracts were washed with brine and saturated aqueous sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e9763ea8365e433ba9448b2738d6e063
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468371B2

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