Triethylamine → HCID 18784728, compound

HRID 1108531Notes

Reaction equation

HRID 1108531 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.Cl.C1(C(C2C=CC=CC=2)=CC[N:41]2[CH2:46][CH2:45][CH:44]([N:47]3[CH2:55][C:54]4[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:48]3=[O:56])[CH2:43][CH2:42]2)C=CC=CC=1>CN(C=O)C.ClCCl>[O:11]=[C:9]([N:41]1[CH2:46][CH2:45][CH:44]([N:47]2[CH2:55][C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:48]2=[O:56])[CH2:43][CH2:42]1)[CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 64798Diphenylpropionic acidHCID 65578Oxalyl chlorideHCID 131720603HCID 131720603, compound

Product 1

HCID 18784728HCID 18784728, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent5×

Procedure

To a solution of 3,3-diphenylpropionic acid (500 mg, 2.21 mmol) and DMF (1 drop) in dichloromethane (5 mL) at RT was added dropwise a solution of oxalyl chloride in dichloromethane (2.0M, 1.66 mL, 3.32 mmol). Bubbling of escaping gasses continued for 10 min after addition. The reaction was stirred at RT for 60 min, then concentrated in vacuo to give a crude oil. To a solution of crude acid chloride and triethylamine (1.4 mL, 10.0 mmol) in dichloromethane (10 mL) at 0° C. under argon was added dropwise a solution of Example 2 Part A compound (434 mg, 2.00 mmol) in dichloromethane (2 mL). The reaction was stirred at 0° C. for 10 min. Dichloromethane (100 mL) was added to dilute the reaction and the resulting solution was washed with H2O (40 mL), saturated sodium bicarbonate solution (40 mL), brine (40 mL) and dried over MgSO4. Evaporation gave a crude gum. Purification was performed by flash chromatography on silica gel (100 g), loaded and eluted with 2.5% methanol in dichloromethane. Pure fractions were combined and evaporated to give title compound (610 mg, 72%) as a off-white solid.

Workup

  1. customBubbling of escaping gasses
  2. additionafter addition
  3. concentrationconcentrated in vacuo
  4. customto give a crude oil
  5. stirringThe reaction was stirred at 0° C. for 10 min
  6. additionto dilute
  7. customthe reaction
  8. washthe resulting solution was washed with H2O (40 mL), saturated sodium bicarbonate solution (40 mL), brine (40 mL)
  9. dry with materialdried over MgSO4
  10. customEvaporation
  11. customgave a crude gum
  12. customPurification
  13. washeluted with 2.5% methanol in dichloromethane
  14. customevaporated

Sources & evidence

ORD record
ord-a9336dbb2e074bd5b972ce640b0ffc4c
Source dataset
uspto-grants-2000_05
Patent number
US06066650

Reaction notes

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