Triethylamine → HCID 58778667, compound

HRID 1372577Notes

Reaction equation

HRID 1372577 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]([OH:21])=O)[CH:15]=[CH:14][C:12]=2[N:13]=1.[C:22]([O:25][C@@H:26]1[CH2:30][NH:29][C@H:28]([CH2:31][O:32][C:33]2[CH:41]=[CH:40][C:36]([C:37]([O-:39])=[O:38])=[CH:35][CH:34]=2)[CH2:27]1)(=[O:24])[CH3:23].[CH3:42]CN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[C:22]([O:25][C@@H:26]1[CH2:30][N:29]([C:19](=[O:21])[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:28]([CH2:31][O:32][C:33]2[CH:34]=[CH:35][C:36]([C:37]([O:39][CH3:42])=[O:38])=[CH:40][CH:41]=2)[CH2:27]1)(=[O:24])[CH3:23]

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 86592797HCID 86592797, compound

Product 1

HCID 58778667HCID 58778667, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (10 ml), a mixture of 2-(2-methylphenylamino)-6-benzoxazolylacetic acid (318 mg, 1.13 mmol), 4-((2S,4S)-4-acetoxy-2-pyrrolidinylmethoxy)benzoate (330 mg, 1.13 mmol), EDC•HCl (325 mg, 1.70 mmol), HOBt (230 mg, 1.70 mmol) and triethylamine (1.18 ml, 8.50 mmol) was stirred at room temperature for 21 hours. The reaction mixture was poured in ice water (30 ml), followed by extraction with ethyl acetate. The extract was washed with 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: 40 g), whereby from chloroform/acetone (20/1) eluate fractions, the title compound (610 mg, 97%) was obtained as a colorless amorphous substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with 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: 40 g), whereby from chloroform/acetone (20/1) eluate fractions

Sources & evidence

ORD record
ord-3d8c89ffc1e2408eb3627d9077617b6e
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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