Triethylamine → HCID 58778392, compound

HRID 1372591Notes

Reaction equation

HRID 1372591 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.[O:22]([C@@H:29]1[CH2:33][NH:32][C@H:31]([CH2:34][O:35][C:36]2[CH:45]=[CH:44][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][CH:37]=2)[CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[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]([N:32]3[CH2:33][C@@H:29]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:30][C@H:31]3[CH2:34][O:35][C:36]3[CH:37]=[CH:38][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:44][CH:45]=3)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=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 58779093HCID 58779093, compound

Product 1

HCID 58778392HCID 58778392, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (10 ml), a mixture of 2-(2-methylphenylamino)-6-benzoxazolylacetic acid (351 mg, 1.07 mmol), methyl 4-((2S,4S)-4-phenoxy-2-pyrrolidinylmethoxy)benzoate (303 mg, 1.07 mmol), EDC•HCl (308 mg, 1.61 mmol), HOBt (218 mg, 1.61 mmol) and triethylamine (0.74 ml, 5.35 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 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: 40 g), whereby from chloroform/acetone (10/1) eluate fractions, the title compound (640 mg, 100%) 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 was purified by chromatography on a silica gel column (silica gel: 40 g), whereby from chloroform/acetone (10/1) eluate fractions

Sources & evidence

ORD record
ord-24d6fd27ec1f4277891d9aae812394c4
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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