Ethyl bromoacetate → HCID 59656591, Verbindung

HRID 2054757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2054757
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([C@@H:16]([NH2:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]=1.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(N(CC)C(C)C)(C)C>CCCCO>[C:17]([C@H:16]([NH:21][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:14]([N:12]1[CH2:13][C:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])=[CH:10][C@H:11]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 24901496HCID 24901496, Verbindung

Produkt 1

HCID 59656591HCID 59656591, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A solution of (1S)-1-{[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]carbonyl}-2,2-dimethylpropylamine (6-1, 325 mg, 0.877 mmol, 1 equiv), ethyl bromoacetate (0.195 mL, 1.76 mmol, 2.00 equiv), and N,N-diisopropylethylamine (0.613 mL, 3.51 mmol, 4.00 equiv) in n-BuOH (4.0 mL) was heated under microwave irradiation at 150° C. for 15 min. The reaction mixture was concentrated and the residue was partitioned between a ethyl acetate (100 mL) and a 1:1 mixture of saturated aqueous potassium bisulfate solution and brine (100 mL). The organic layer was then washed with saturated aqueous sodium bicarbonate solution (100 mL) followed by brine (100 mL), then dried over magnesium sulfate and concentrated to give ethyl ({(1S)-1-tert-butyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethyl}amino)acetate (7-1) as an off-white solid. LRMS m/z (M+H) 457.5 found, 457.2 required.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between a ethyl acetate (100 mL)
  3. additiona 1:1 mixture of saturated aqueous potassium bisulfate solution and brine (100 mL)
  4. washThe organic layer was then washed with saturated aqueous sodium bicarbonate solution (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5884c74d3d9a4ee4acd19679cc880582
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07329762B2

Notizen zur Reaktion

Wird geladen…