Triethylamine → HCID 88495351, compound

HRID 654540Notes

Reaction equation

HRID 654540 reaction equation
[OH:1][CH:2]([CH2:7][CH:8](O)/[CH:9]=[CH:10]/[C:11]1[C:21]([CH3:23])([CH3:22])[CH2:20][C:14]2([S:19][CH2:18][CH2:17][CH2:16][S:15]2)[CH2:13][C:12]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[C:26]([CH3:31])[CH:25]=1)[CH2:3][C:4]([OH:6])=[O:5].C(N(CC)CC)C.ClC(OCC)=O>C(Cl)Cl.CCOCC>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:12]2[CH2:13][C:14]3([CH2:20][C:21]([CH3:23])([CH3:22])[C:11]=2/[CH:10]=[CH:9]/[C@@H:8]2[O:5][C:4](=[O:6])[CH2:3][C@@H:2]([OH:1])[CH2:7]2)[S:19][CH2:18][CH2:17][CH2:16][S:15]3)=[CH:25][C:26]=1[CH3:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 19887536HCID 19887536, compound

Product 1

HCID 88495351HCID 88495351, compoundYield 70.5%

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. C23H31FO3S2 : Theory C: 64.91; H: 6.75. Found C: 65.31; 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-c963e68fed3442b78815317501fd4f56
Source dataset
uspto-grants-1992_07
Patent number
US05132312

Reaction notes

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