Chloroacetyl isocyanate → Benzhydryl (E)-(2S,3S,5R)-3-[3-(2-chloro-acetylamino-carbonyloxy)-propenyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

HRID 263754

Reaktionsgleichung

Reaktionsgleichung von HRID 263754
[OH:1][CH2:2]/[CH:3]=[CH:4]/[C@:5]1([CH3:29])[S:11][C@H:10]2[N:7]([C:8](=[O:12])[CH2:9]2)[C@H:6]1[C:13]([O:15][CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].[Cl:30][CH2:31][C:32]([N:34]=[C:35]=[O:36])=[O:33]>O1CCCC1>[Cl:30][CH2:31][C:32]([NH:34][C:35]([O:1][CH2:2]/[CH:3]=[CH:4]/[C@:5]1([CH3:29])[S:11][C@H:10]2[N:7]([C:8](=[O:12])[CH2:9]2)[C@H:6]1[C:13]([O:15][CH:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:14])=[O:36])=[O:33]

Komponenten

4

Edukt 2

HCID 78209Chloroacetyl isocyanateHCID 10645194benzhydryl (E)-(2S,3S,5R)-3-(3-hydroxy-propenyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Produkt 1

HCID 10506359Benzhydryl (E)-(2S,3S,5R)-3-[3-(2-chloro-acetylamino-carbonyloxy)-propenyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

300 mg (0.73 mmol) of benzhydryl (E)-(2S,3S,5R)-3-(3-hydroxy- propenyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 10 ml of tetrahydrofuran under argon and treated with 90 μl (1.05 mmol) of chloroacetyl isocyanate. The mixture was stirred for 3 hours, evaporated and chromatography was carried out over silica gel (particle size 0.040-0.063 mm) with ethyl acetate:n-hexane (9:16) as the eluent. Yield: 300 mg (77%) of colorless foam IR (KBr): 3300(br), 1779, 1753, 1730, 1495, 1203 cm-1MS: (M+NH4)+ 546.4

Aufarbeitung

  1. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8ec3bf806a064b2c9df0a3009a253ecf
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05644053

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