Triethylamine → HCID 178521402, compound

HRID 129538Notes

Reaction equation

HRID 129538 reaction equation
[CH2:1]1[C:6](=[O:7])[S:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.[CH:15]1([O:27][CH2:28][C:29](O)=[O:30])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+]1(CCN=C=NC2CCCCC2)CCOCC1.[K+].[Br-]>ClCCl.CN(C)C1C=CN=CC=1>[CH:15]1([O:27][CH2:28][C:29]([C:1]2[C:6](=[O:7])[S:5][CH2:4][C:2]=2[OH:3])=[O:30])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 253877Potassium BromideHCID 10214383Thiotetronic acidHCID 193718122-(Cyclododecyloxy)acetic acid

Product 1

HCID 178521402HCID 178521402, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.37 g (3.2 mmol) of thiotetronic acid in 20 mL of dry dichloromethane at 0° C. is added 0.4 mL (2.9 mmol) of triethylamine followed by 0.11 g (0.9 mmol) of 4-dimethylaminopyridine. After stirring at 0° C. for 5 minutes, 0.7 g (2.9 mmol) of cyclododecyloxyacetic acid is added, followed by 1.35 g (3.2 mmol) of 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate. After 10 minutes the ice bath is removed and the reaction mixture is allowed to stir overnight. The reaction mixture is quenched with 1N HCl. The layers are separated and the organic layer is washed twice with aqueous sodium bicarbonate and then twice with 2N HCl. The organic phase is then dried over MgSO4 and the dichloromethane evaporated. The residue is flash chromatographed on acidic silica gel using 50% ether/hexanes and then recrystallized from hexanes to give a yellow solid: m.p. 93°-95° C.; IR (KBr) 2920, 2840, 1690, 1660, 1580 cm-1 ; NMR (DMSO-d6) δ 1.2-1.6 (m, 10H), 3.4 (m, 1H), 3.95 and 4.4 (s, 2H), 4.6 (bs, 2H); MS (EI) M+ 340.

Workup

  1. customAfter 10 minutes the ice bath is removed
  2. stirringto stir overnight
  3. customThe reaction mixture is quenched with 1N HCl
  4. customThe layers are separated
  5. washthe organic layer is washed twice with aqueous sodium bicarbonate
  6. dry with materialThe organic phase is then dried over MgSO4
  7. customthe dichloromethane evaporated
  8. customchromatographed on acidic silica gel using 50% ether/hexanes
  9. customrecrystallized from hexanes
  10. customto give a yellow solid

Sources & evidence

ORD record
ord-91892274a5a94765948a1636bcbe7d32
Source dataset
uspto-grants-1995_11
Patent number
US05468774

Reaction notes

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