Triethylamine → 5-(4-{4-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-phenyl)-pent-4-ynoic acid

HRID 1253766Notes

Reaction equation

HRID 1253766 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11](=[O:26])[NH:12][C:13]1[C:14]([CH3:25])=[N:15][O:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=1)[CH3:9].[C:27]([OH:33])(=[O:32])[CH2:28][CH2:29][C:30]#[CH:31].C(N(CC)CC)C>COCCOC.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]([NH:12][C:13]1[C:14]([CH3:25])=[N:15][O:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([C:31]#[C:30][CH2:29][CH2:28][C:27]([OH:33])=[O:32])=[CH:20][CH:19]=1)=[O:26])[CH3:9]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 224644-Pentynoic acidHCID 67350786[5-(4-Bromophenyl)-3-methylisoxazol-4-yl]carbamic acid 1-(2-chlorophenyl)ethyl ester

Product 1

HCID 462139065-(4-{4-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-phenyl)-pent-4-ynoic acid

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid 1-(2-chloro-phenyl)-ethyl ester (0.200 g, 0.46 mmol), 4-pentynoic acid (0.054 g, 0.55 mmol), copper iodide (spatula tip), triethylamine (0.12 mL, 0.84 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.053 g, 0.05 mmol) were combined in DME (5 mL), and the reaction was purged with N2 for 15 minutes and then stirred at 80° C. overnight. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was separated and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by preparative HPLC to give the title compound. Mass spec. data (M+H)=453.

Workup

  1. customthe reaction was purged with N2 for 15 minutes
  2. customThe mixture was partitioned between EtOAc and H2O
  3. customthe aqueous layer was separated
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-ada0a0b0b2aa4defb6813a30a6aa2f2f
Source dataset
uspto-grants-2013_06
Patent number
US08455499B2

Reaction notes

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