Hydrochloric Acid → methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)carbamate

HRID 233339

Reaktionsgleichung

Reaktionsgleichung von HRID 233339
C([Li])CCCCC.[CH3:8][O:9][C:10]([NH:12][C@@H:13]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:14]([O:16]C)=O)=[O:11].Cl[Si](C)(C)C.Br[CH2:31][Cl:32].Cl>CCCCCC.O1CCCC1.O>[CH2:18]([C@H:13]([NH:12][C:10](=[O:11])[O:9][CH3:8])[C:14](=[O:16])[CH2:31][Cl:32])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 6333BromochloromethaneHCID 6397ChlorotrimethylsilaneHCID 10609905(S)-Methyl 2-((methoxycarbonyl)amino)-3-phenylpropanoateHCID 178506865HCID 178506865, Verbindung2×

Produkt 1

HCID 9881533methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)carbamateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

15.4 ml of a 2.6 molar solution of hexyllithium in hexane were added dropwise at -80° C. to a solution of 9.50 g of methyl (S)-2-methoxycarbonylamino-3-phenyl-propionate in 60 ml of tetrahydrofuran. Subsequently, the mixture was treated with 5.60 ml of chlorotrimethylsilane. The resulting suspension was stirred and treated with 3.22 ml of bromochloromethane. Subsequently, 18.4 ml of hexyllithium solution were added. The solution was treated at -80° C. with 11 ml of 20% methanolic hydrochloric acid, warmed to 22° and diluted with 100 ml of water and 40 ml of tetrahydrofuran. The phases were separated and the organic phase was washed with saturated sodium chloride solution, dried and concentrated. The residue was recrystallized from ethyl acetate and hexane and the crystallizate was dried, there being obtained 7.20 g (70%) of pure methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)-carbamate, m.p. 122°-123° C. IR (KBr): 3336s (NH), 1737s and 1686s (C=O), 1535s (amide II).

Aufarbeitung

  1. temperaturewarmed to 22°
  2. customThe phases were separated
  3. washthe organic phase was washed with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethyl acetate and hexane
  7. customthe crystallizate was dried

Quellen und Nachweise

ORD-Eintrag
ord-9bef9ffaabdf42c7983198d7d20b557d
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591885

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