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Potassium Carbonate → 3-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2,5-dione

HRID 482743
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 482743
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[NH:11][C:10]1=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(N)=C(C(C[C@H](N)C(O)=O)=O)C=1.Br[CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]([CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:10]1=[O:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]
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Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 161166KynurenineHCID 14666415tert-Butyl (S)-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)carbamate

Produkt 1

HCID 100926163-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 3-(S)-t-butyloxycarbonylamino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2,5-dione (12.5 g) prepared from L-kynurenine as described in Australian J. Chemistry Vol. 33, 633-40 (1980), and t-butyl bromoacetate (10.1 g) in acetone (700 ml) was stirred at room temperature under a dry nitrogen atmosphere. Potassium carbonate (12.5 g) was added in one portion and the resulting suspension was stirred at room temperature for 16 hours. The potassium salts were filtered off and the filtrate evaporated to dryness. The residue was partitioned between ethyl acetate (250 ml) and H2O (250 ml). The layers were separated and the organic phase dried (sodium sulfate). The residue was triturated with petroleum ether (350 ml; bp 30°-60°) to give 3-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2,5-dione, m.p. 75°-77° C., [alpha]D =-172° (C=0.96 in DMF).

Aufarbeitung

  1. filtrationThe potassium salts were filtered off
  2. customthe filtrate evaporated to dryness
  3. customThe residue was partitioned between ethyl acetate (250 ml) and H2O (250 ml)
  4. customThe layers were separated
  5. dry with materialthe organic phase dried (sodium sulfate)
  6. customThe residue was triturated with petroleum ether (350 ml; bp 30°-60°)

Quellen und Nachweise

ORD-Eintrag
ord-faff96c0a9a640b2b1b20dd72270d430
Quelldatensatz
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04575503

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