Boron trifluoride etherate → HCID 15123251, compound

HRID 1196524Notes

Reaction equation

HRID 1196524 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([N:13]2[CH2:18][CH2:17]C(=O)C[CH:14]2[CH2:20][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9].[CH:26]([SH:29])([SH:28])[CH3:27].B(F)(F)F.[CH3:34][CH2:35]OCC.[OH-].[Na+]>ClCCl>[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([N:13]2[CH2:18][CH2:17][C:26]3([S:29][CH2:35][CH2:34][S:28]3)[CH2:27][CH:14]2[CH2:20][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 336451,1-EthanedithiolHCID 19898849HCID 19898849, compound

Product 1

HCID 15123251HCID 15123251, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 8 (0.25 g) and ethanedithiol (0.1 ml) in dry dichloromethane (5 ml) at 0°-5° was treated with borontrifluoride etherate (0.020 ml, 0.16 mmol). The mixture was stirred at ambient temperature for 18 h. Aqueous sodium hydroxide (2M; 5 ml) was added and the product was extracted with dichloromethane (2×15 ml). The combined extracts were dried and evaporated to give an oily residue, which was purified by flash chromatography eluting with dichloromethane/methanol/ammonia 200:8:1 to give a solid which was crystallized from a mixture of methylacetate and hexane to give the title compound as a solid (0.155 g) m.p. 119°-20°. T.l.c. SiO2Dichloromethane/methanol/ammonia 150:10:2 Rf 0.7.

Workup

  1. extractionthe product was extracted with dichloromethane (2×15 ml)
  2. customThe combined extracts were dried
  3. customevaporated
  4. customto give an oily residue, which
  5. customwas purified by flash chromatography
  6. washeluting with dichloromethane/methanol/ammonia 200:8:1
  7. customto give a solid which
  8. customwas crystallized from a mixture of methylacetate and hexane

Sources & evidence

ORD record
ord-4919dac10dcf46378710488b3121a50e
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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