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Ethyl bromoacetate → HCID 15870967, Verbindung

HRID 2414802
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2414802
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23](=[O:25])[CH3:24])(=[O:21])=[O:20])=[CH:15][CH:14]=1.Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].CCN(CC)CC>ClCCl>[C:23]([N:22]([S:19]([C:16]1[CH:17]=[CH:18][C:13]([C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:14][CH:15]=1)(=[O:20])=[O:21])[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])(=[O:25])[CH3:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetate2×HCID 8471Triethylamine2×HCID 10833494N-((4-(5-Methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)acetamide

Produkt 1

HCID 15870967HCID 15870967, VerbindungAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel
2×

Versuchsvorschrift

To a stirred solution of N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]acetamide (Example 39) (0.612 g, 1.72 mmol) in dichloromethane was treated with ethyl bromoacetate (0.20 mL, 0.29 g, 1.72 mmol) and Et3N (0.26 mL, 0.19 g, 1.89 mmol). After 7 days the reaction was still incomplete by TLC. Additional ethyl bromoacetate (0.20 mL, 0.29 g, 1.72 mmol) and Et3N (0.26 mL, 0.19 g, 1.89 mmol) were added and the reaction was stirred for an additional 6 days. The reaction was diluted with dichloromethane and washed with KHSO4 solution, NaHCO3 solution, and brine, dried over MgSO4, filtered and concentrated in vacuo yielding a clear oil. This oil was purified by flash chromatography yielding N-acetyl-N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]glycine, ethyl ester (0.243 g, 32%) as a clear colorless oil of suitable purity for use in the next step: 1H NMR (CDCl3/300 MHz) 8.03 (d, 2H, J=8.7 Hz), 7.47-7.27 (m, 9H), 4.61 (s, 2H), 4.21 (q, 2H, J=7.1 Hz), 2.51 (s, 3H), 2.33 (s, 3H), 1.28 (t, 3H, J=7.1 Hz). FABLRMS m/z 443 (M+H). FABHRMS m/z 442.1201 (M+, C22H22N2O6S Calc'd 442.1199).

Aufarbeitung

  1. washwashed with KHSO4 solution, NaHCO3 solution, and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customyielding a clear oil
  6. customThis oil was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-17a11c8236694c73b5aebe695ba4315c
Quelldatensatz
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06815460B2

Notizen zur Reaktion

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