Triethylamine → HCID 59696201, compound

HRID 900335Notes

Reaction equation

HRID 900335 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:15][O:16][C:17](=[O:48])[CH:18]([NH2:47])[CH2:19][S:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[C:39]4[O:40][C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=5[C:38]=4[CH:37]=[CH:36][CH:35]=3)=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>O.C(Cl)Cl>[CH3:15][O:16][C:17](=[O:48])[CH:18]([NH:47][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:2]=1[F:1])[CH2:19][S:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:29]=[CH:30][C:31]([C:34]3[C:39]4[O:40][C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=5[C:38]=4[CH:37]=[CH:36][CH:35]=3)=[CH:32][CH:33]=2)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6882922-Fluoro-5-(trifluoromethyl)benzoic acidHCID 59696193HCID 59696193, compound

Product 1

HCID 59696201HCID 59696201, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-5-trifluoromethylbenzoic acid (49 mg, 0.24 mmol) was added to a stirred solution of methyl-2-amino-3-(4′-dibenzofuran-4-ylbipheny-4-ylmethylsulfanyl)-propionate (92 mg, 0.2 mmol), EDCI (58 mg, 0.3 mmol) and triethylamine (404 mg, 0.56 mL, 0.4 mmol) in anhyd methylene chloride (5 mL). The reaction mixture was stirred at room temperature for 4-6 h (TLC control) and then diluted with water (10 mL). The reaction mixture was extracted with ethyl acetate (2×20 mL). The combined organic extract were washed with water, sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (30% ethyl acetate in heptane) afforded the title compound has a white solid (117 mg).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×20 mL)
  2. extractionThe combined organic extract
  3. washwere washed with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography (30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-3ce93be0e265481cacccbda85a5de764
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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