Reaktion #507446

ord-90f4d31b6ed74d3098faf2a09a833331

Reaktionsgleichung

CCCCCC.CCOC(C)=O
hexane EtOAc
C=CCOC(=O)C1CSCC(NC(=O)OC(C)(C)C)C1=O
5-tert-butoxycarbonylamino-4-oxo-tetrahydro-thiopyran-3-carboxylic acid allyl ester
O=C([O-])[O-].[K+].[K+]
K2CO3
O=[N+]([O-])c1ccc(CBr)cc1F
4-bromomethyl-2-fluoro-1-nitro-benzene
→
C=CCOC(=O)C1(Cc2ccc([N+](=O)[O-])c(F)c2)CSCC(NC(=O)OC(C)(C)C)C1=O
5-tert-Butoxycarbonylamino-3-(3-fluoro-4-nitro-benzyl)-4-oxo-tetrahydro-thiopyran-3-carboxylic acid allyl ester

Edukte

CCCCCC.CCOC(C)=O
hexane EtOAc
C=CCOC(=O)C1CSCC(NC(=O)OC(C)(C)C)C1=O
5-tert-butoxycarbonylamino-4-oxo-tetrahydro-thiopyran-3-carboxylic acid allyl ester
O=C([O-])[O-].[K+].[K+]
K2CO3
O=[N+]([O-])c1ccc(CBr)cc1F
4-bromomethyl-2-fluoro-1-nitro-benzene

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Temperatur
25°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    ExtraktionAfter dilution with water the product is extracted with EtOAc
  2. 2
    WaschenCombined extracts were washed with brine
  3. 3
    Trocknendried over MgSO4
  4. 4
    Sonstigeevaporated
  5. 5
    SonstigeThe product obtained as a light yellow solid
  6. 6
    SonstigeHPLC RtA=2.31 min

Vorschrift

To a solution of 5-tert-butoxycarbonylamino-4-oxo-tetrahydro-thiopyran-3-carboxylic acid allyl ester (2.55 g, 8.08 mmol) in acetone (150 mL) was added K2CO3 (3.38 g, 24.2 mmol) and 4-bromomethyl-2-fluoro-1-nitro-benzene (2.12 g, 8.9 mmol) and the reaction mixture was stirred at 25° C. for 16 h. After dilution with water the product is extracted with EtOAc. Combined extracts were washed with brine, dried over MgSO4 and evaporated. The product obtained as a light yellow solid was suitable for use in the next step: TLC (hexane-EtOAc 1:3) Rf=0.26; HPLC RtA=2.31 min; ESIMS [M+NH4]+=486.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08093406B2uspto-grants-2012_01