Triethylamine → HCID 69417847, compound

HRID 1372627Notes

Reaction equation

HRID 1372627 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16](CC(O)=O)[CH:15]=[CH:14][C:12]=2[N:13]=1.[F:22][C@@H:23]1[CH2:27][NH:26][C@H:25]([CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O-:37])=[O:36])[CH2:24]1.[CH3:38]CN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[F:22][C@@H:23]1[CH2:27][N:26]([C:16]2[CH:15]=[CH:14][C:12]3[N:13]=[C:9]([NH:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])[O:10][C:11]=3[CH:17]=2)[C@H:25]([CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:24]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235083152-(2-(O-tolylamino)benzo[d]oxazol-6-yl)acetic acidHCID 86760352HCID 86760352, compound

Product 1

HCID 69417847HCID 69417847, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (10 ml), 2-(2-methylphenylamino)-6-benzoxazolylacetic acid (282 mg, 1.00 mmol), 6-((2S,4S)-4-fluoro-2-pyrrolidinylmethoxy)hexanoate (247 mg, 1.00 mmol), EDC•HCl (288 mg, 1.50 mmol), HOBT (203 mg, 1.50 mmol) and triethylamine (0.70 ml, 5.00 mmol) were stirred at room temperature for 22 hours. The reaction mixture was poured in ice water (50 ml), followed by extraction with ethyl acetate. The extract was washed with ice water and saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue thus obtained was purified by thin-layer silica gel chromatography, followed by separation by using chloroform/acetone (10/1), whereby the title compound (330 mg, 65%) was obtained as a yellow oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with ice water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue thus obtained
  7. customwas purified by thin-layer silica gel chromatography
  8. customfollowed by separation
  9. customwas obtained as a yellow oil

Sources & evidence

ORD record
ord-21b6efb3bc764edcb5c8046868974a29
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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