Ethyl Acetate → HCID 178473725, compound

HRID 849425Notes

Reaction equation

HRID 849425 reaction equation
Cl.Cl.Cl.[NH:4]1[CH:8]=[C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]4[CH:22]=N[CH:24]=[CH:25][CH:26]=4)=[CH:20][C:15]=3[CH2:14][N:13]([C:27](=[O:32])[C:28](F)(F)F)[CH:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:11]2)[N:6]=[CH:5]1.[Sn](Cl)[Cl:41].[C:43](OCC)(=O)C>>[ClH:41].[C:27]([N:13]1[CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:22]=[CH:43][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][C:16]=2[N:10]([CH2:9][C:7]2[N:6]=[CH:5][NH:4][CH:8]=2)[CH2:11][C@H:12]1[CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)(=[O:32])[CH3:28]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 24479Stannous ChlorideHCID 178478619HCID 178478619, compound

Product 1

HCID 178473725HCID 178473725, compoundYield 52%

Procedure

A mixture of Compound B (660 mg, 1.68 mmol), tin (II) chloride (1.52 g, 6.7 mmol) and ethyl acetate (75 mL) was stirred at room temperature for 18 hours and quenched with aqueous and then solid potassium carbonate (5 mL, then 5 gms). The mixture was filtered, the filtrate partitioned and the organic phase dried (MgSO4), concentrated in vacuum, and purified using flash chromatography (3:1 hexane:ethyl acetate) to provide Compound C (315 mg, 52%) as a clear oil.

Workup

  1. customquenched with aqueous and then solid potassium carbonate (5 mL
  2. filtrationThe mixture was filtered
  3. customthe filtrate partitioned
  4. dry with materialthe organic phase dried (MgSO4)
  5. concentrationconcentrated in vacuum
  6. custompurified

Sources & evidence

ORD record
ord-68c0a6e5f2b94757874d08b924a83cff
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

Loading…