Methyl bromoacetate → HCID 54305290, Verbindung

HRID 502325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502325
[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:11](=[O:12])[C@@H:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][NH:8][C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]1=2.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(OC(NC1C(=O)NC2C=CC=CC=2NC1)=O)(C)(C)C.BrCC(OC)=O>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:11](=[O:12])[CH:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:9][NH:8][C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]1=2

Komponenten

7

Edukt 4

HCID 60984Methyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 154908313-Tert-butoxycarbonylamino-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-oneHCID 54305289(3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

Produkt 1

HCID 54305290HCID 54305290, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(3(S)-tert-Butoxycarbonylamino-2-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)acetic acid methyl ester (103). A 1.0 M solution of lithium bis(trimethylsilyl)amide (3.4 ml, 3.4 mmol) in THF was added dropwise to a −78° C. solution of 3-tert-butoxycarbonylamino-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-one (0.94 g, 3.38 mmol) in 20 ml of anhydrous tetrahydrofuran and stirred for 30 minutes. Methyl bromoacetate (0.44 ml, 4 mmol) was added dropwise to the reaction mixture then warmed to room temperature. The reaction was diluted with 100 ml of ethyl acetate and washed with 0.3N potassium hydrogen sulfate (50 ml), water (2×50 ml), and brine. The combined organics were dried over anhydrous sodium sulfate, filtered, and evaporated to afford a gum that was purified by flash chromatography eluting with 3:7 EtOAc/Hex. to give 0.98 g (83%) of the title compound as a white solid. 1H NMR (CDCl3) δ 7.15-7.07 (2H, m), 6.98-6.94 (1H, m), 6.88-6.84 (1H, d), 5.62-5.55 (1H, d), 4.71-4.65 (1H, d), 4.65-4.6 (1H, m), 4.33-4.27 (1H, d), 3.96-3.90 (1H, m), 3.78 (3H, s), 3.44-3.37 (1H, m), 1.4 (9H, s).

Aufarbeitung

  1. washwashed with 0.3N potassium hydrogen sulfate (50 ml), water (2×50 ml), and brine
  2. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto afford a gum that
  6. customwas purified by flash chromatography
  7. washeluting with 3:7 EtOAc/Hex

Quellen und Nachweise

ORD-Eintrag
ord-57399eb203344c3f8dac98cef634a149
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772366B2

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