Triethylamine → HCID 15125260, compound

HRID 359560Notes

Reaction equation

HRID 359560 reaction equation
OC(CC(O)/C=C/[C:11]1[C:21]([CH3:23])([CH3:22])[CH2:20][C:14]2(SCCCS2)[CH2:13][C:12]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[C:26]([CH3:31])[CH:25]=1)CC(O)=O.C(N(CC)CC)C.Cl[C:41]([O:43][CH2:44]C)=[O:42]>C(Cl)Cl.CCOCC>[CH3:23][C:21]1([CH3:22])[CH2:20][CH2:14][CH:13]=[C:12]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([CH3:31])[CH:25]=2)[CH:11]1[C:41]([O:43][CH3:44])=[O:42]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 19887536HCID 19887536, compound

Product 1

HCID 15125260HCID 15125260, compoundYield 118%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a 0°-5° C. solution of 12 (0.90 gm, 1.87 mmol) and triethylamine (315 μL, 2.25 mmol) in 10 mL CH2Cl2 was added dropwise ethyl chloroformate (185 μL, 1.87 mmol). The mixture was stirred for 30 min, diluted with ether, washed with H2O, saturated NaHCO3 and brine and dried (MgSO4). Removal of the volatiles in vacuo and purification of the residue by SiO2 using 3:2 hexanes:EtOAc as eluent provided 0.61 g of the product. mp 136°-8° C. Anal. C25H31FO3S2 : Theory C: 64.91; H: 6.75. Found C: 65.3I; H: 6.82.

Workup

  1. washwashed with H2O, saturated NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. customRemoval of the volatiles
  4. customin vacuo and purification of the residue by SiO2 using 3:2 hexanes

Sources & evidence

ORD record
ord-607e2fa23b1645bb8a5230071a2d284e
Source dataset
uspto-grants-1991_03
Patent number
US05001144

Reaction notes

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