Water → 3,5-dimethyl-4-([1,4]oxazepane-4-sulfonyl)-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 2375805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375805
Cl.[O:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[CH2:18]([O:20][C:21]([C:23]1[NH:24][C:25]([CH3:33])=[C:26]([S:29](Cl)(=[O:31])=[O:30])[C:27]=1[CH3:28])=[O:22])[CH3:19].O>C(Cl)Cl>[CH2:18]([O:20][C:21]([C:23]1[NH:24][C:25]([CH3:33])=[C:26]([S:29]([N:5]2[CH2:6][CH2:7][CH2:8][O:2][CH2:3][CH2:4]2)(=[O:30])=[O:31])[C:27]=1[CH3:28])=[O:22])[CH3:19]

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2776544ethyl 4-(chlorosulfonyl)-3,5-dimethyl-1H-pyrrole-2-carboxylateHCID 230902141,4-Oxazepane hydrochloride

Produkt 1

HCID 692881593,5-dimethyl-4-([1,4]oxazepane-4-sulfonyl)-1H-pyrrole-2-carboxylic acid ethyl esterAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To [1,4]oxazepane hydrochloride (400 mg) in DCM (45 mL) was added DIEA (2.70 mL) followed by 4-chlorosulfonyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.05 g). The mixture was stirred for 1 h at RT after which water was added and the resulting two phases were separated. The organic phase was washed two times with saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated to give crude) 3,5-dimethyl-4-([1,4]oxazepane-4-sulfonyl)-1H-pyrrole-2-carboxylic acid ethyl ester (970 mg) which was used directly in the following step.

Aufarbeitung

  1. additionwas added
  2. customthe resulting two phases were separated
  3. washThe organic phase was washed two times with saturated aqueous NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e88dcafadfa04c56af0a42dc2674c4ef
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465806B2

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