Triethylamine → HCID 69742483, compound

HRID 458462Notes

Reaction equation

HRID 458462 reaction equation
C([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[C:18](C(OCC)=O)=[C:17]([C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)[C:16]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:15]([CH2:38][CH2:39][C:40]([F:43])([F:42])[F:41])[N:14]=1)=O)(C)(C)C.C(N(CC)CC)C>OC(C(F)(F)F)=O.ClCCl.ClCCl>[CH2:36]([O:35][C:33]([C:16]1[C:15]([CH2:38][CH2:39][C:40]([F:41])([F:43])[F:42])=[N:14][C:13]2[C@H:9]3[N:8]([C:6](=[O:5])[C:18]=2[C:17]=1[C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)[CH2:12][CH2:11][CH2:10]3)=[O:34])[CH3:37]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 69516070HCID 69516070, compound

Product 1

HCID 69742483HCID 69742483, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To a stirred solution of 4-[2-[(2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinyl]-3,5-bis(ethoxycarbonyl)-6-(3,3,3-trifluoropropyl)-4-pyridinyl]benzoic acid (3.0 g, 4.93 mmol) dissolved in 30 mL of dichloromethane TFA (7 mL) was added. The reaction stirred for 1.5 h. and was then concentrated to yield a reddish brown oil. The crude mixture was dissolved in 35 mL of dichloromethane and triethylamine (10 mL) was added slowly. The reaction was allowed to stir overnight. The mixture was then concentrated and redissolved in 50 mL of ethyl acetate. The organics were washed with 1 M HCl, H2O and Brine. The organics were then dried over sodium sulfate, filtered and concentrated. The concentrated material was purified by column chromatography (dichloromethane/MeOH (20:1)) to yield 0.928 g (41%) of the desired product as an off white solid.

Workup

  1. additionwas added
  2. concentrationwas then concentrated
  3. customto yield a reddish brown oil
  4. stirringto stir overnight
  5. concentrationThe mixture was then concentrated
  6. dissolutionredissolved in 50 mL of ethyl acetate
  7. washThe organics were washed with 1 M HCl, H2O and Brine
  8. dry with materialThe organics were then dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe concentrated material was purified by column chromatography (dichloromethane/MeOH (20:1))

Sources & evidence

ORD record
ord-c1c357335d154a35ac7c641903680e90
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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