Water → 1,1-Dimethylethyl 2-bromo-4,5,7,8-tetrahydro-6H-thieno[2,3-d]azepine-6-carboxylate

HRID 2237430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2237430
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][S:17][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:18]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([Br:18])[S:17][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 57354994tert-Butyl 4,5,7,8-tetrahydro-6H-thieno[2,3-d]azepine-6-carboxylate

Produkt 1

HCID 593025511,1-Dimethylethyl 2-bromo-4,5,7,8-tetrahydro-6H-thieno[2,3-d]azepine-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584526Acetic acid chloroformLösungsmittel

Versuchsvorschrift

The product of step f) (10 mg, 0.039 mmol) dissolved in a 50:50 mixture of chloroform/acetic acid (1 ml) was treated with N-bromosuccinimide (7 mg, 0.041 mmol). The reaction mixture was stirred for 30 minutes at ambient temperature. The reaction mixture was poured into water (5 ml) and extracted with CHCl3 (3×5 ml). The combined organic phases were washed with 10% KOH solution (5 ml), brine (5 ml), dried (MgSO4), and concentrated to give the crude product as an oil. Purification by HPLC gave the subtitle compound as an oil. MS: ESI (positive): 332, 334 (M+H).

Aufarbeitung

  1. extractionextracted with CHCl3 (3×5 ml)
  2. washThe combined organic phases were washed with 10% KOH solution (5 ml), brine (5 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give the crude product as an oil
  6. customPurification by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6fd29d1d333f488b910518d67c8cf762
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718647B2

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