Triethylamine → HCID 58778519, compound

HRID 1372622Notes

Reaction equation

HRID 1372622 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]([CH2:18][C:19](O)=[O:20])[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][C:34]([O:36][CH3:37])=[O:35])[CH2:24]1.CCN=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:19](=[O:20])[CH2:18][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][C:34]([O:36][CH3:37])=[O:35])[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 58778388HCID 58778388, compound

Product 1

HCID 58778519HCID 58778519, compoundYield 167.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (5 ml), a mixture of 2-(2-methylphenylamino)-6-benzoxazolylacetic acid (357 mg, 1.26 mmol), methyl 5-((2S,4S)-4-fluoro-2-pyrrolidinylmethoxy)pentanoate (295 mg, 1.26 mmol), EDC•HCl (362 mg, 1.89 mmol), HOBt (255 mg, 1.89 mmol) and triethylamine (0.88 ml, 6.30 mmol) was stirred at room temperature for 1 hour. 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 was purified by chromatography on a silica gel column (silica gel: 70 g), whereby from chloroform/acetone (10/1) eluate fractions, the title compound (1.05 g, 100%) was obtained as a colorless 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 was purified by chromatography on a silica gel column (silica gel: 70 g), whereby from chloroform/acetone (10/1) eluate fractions

Sources & evidence

ORD record
ord-1ac6d8fac0cc4269b3f2fa3bc1c18a10
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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