Triethylamine → HCID 59789468, compound

HRID 1013403Notes

Reaction equation

HRID 1013403 reaction equation
[CH:1]1[C:5]2[CH2:6][CH:7]3[CH:12]([C:4]=2[S:3][CH:2]=1)[CH2:11][CH2:10][NH:9][CH2:8]3.C(N(CC)CC)C.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(Cl)Cl>[CH2:24]([O:23][C:21]([N:9]1[CH2:10][CH2:11][CH:12]2[CH:7]([CH2:6][C:5]3[CH:1]=[CH:2][S:3][C:4]=32)[CH2:8]1)=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 862291074,5,6,7,7a,8-Hexahydro-3bH-3-thia-6-aza-cyclopenta[alpha]indene

Product 1

HCID 59789468HCID 59789468, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22 °C

Procedure

A 0° C. solution of the product from step g) (874 mg, 4.05 mmol) in CH2Cl2 (20 ml) was treated with triethylamine (1.69 ml, 12.15 mmol) and ethyl chloroformate (466 μl, 4.86 mmol) and the reaction was warmed to 22° C. Next, the reaction mixture was diluted with CH2Cl2 (50 ml) and washed with brine (25 ml). The organic layer was dried (MgSO4) and solvent evaporated in vacuo leaving the crude product that was purified by silica-gel chromatography (hexanes:EtOAc-50:50) to give 722 mg (71%) of the subtitle compound. MS calculated for C13H17NO2S+H 252, observed 252.

Workup

  1. washwashed with brine (25 ml)
  2. dry with materialThe organic layer was dried (MgSO4) and solvent
  3. customevaporated in vacuo
  4. customleaving the crude product that
  5. customwas purified by silica-gel chromatography (hexanes:EtOAc-50:50)

Sources & evidence

ORD record
ord-fae6aed6e5bc4880b3ac6720b000af47
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

Loading…