Triethylamine → HCID 44511926, compound

HRID 1669981Notes

Reaction equation

HRID 1669981 reaction equation
C([O:5][C:6](=[O:23])[C:7]1[CH:12]=[C:11]([F:13])[C:10]([Cl:14])=[CH:9][C:8]=1[NH:15][C:16]([O:18]C(C)(C)C)=O)(C)(C)C.[O:24]([C:31]1[CH:39]=[CH:38][C:34](C(Cl)=O)=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C1COCC1>[Cl:14][C:10]1[C:11]([F:13])=[CH:12][C:7]([C:6]([OH:5])=[O:23])=[C:8]([NH:15][C:16](=[O:18])[C:34]2[CH:38]=[CH:39][C:31]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:32][CH:33]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 741934-Phenoxybenzoyl chlorideHCID 67352713HCID 67352713, compound

Product 1

HCID 44511926HCID 44511926, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of Argon, 2-tert-butoxycarbonylamino-4-chloro-5-fluoro-benzoic acid tert-butyl ester (200 mg) and 4-phenoxy-benzoyl chloride ([1623-95-6], 269 mg) were dissolved in THF (5 mL). Triethylamine (0.24 ml) was added, and the mixture was heated to reflux overnight. The solvent was evaporated, and the residue was purified by column chromatography (silica gel/methanol/dichloromethane). The eluate, which contained two UV-absorbing components, was evaporated, and the residue was dissolved in a mixture of dichloromethane (0.5 ml) and trifluoroacetic acid (0.5 ml). After 2 h, the volatiles were evaporated, and the title compound (9 mg, 0.4%) was isolated from the mixture by preparative, reversed-phase HPLC (Agilent Zorbax XdB C18 column, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 4.5 min, flow rate 30 ml/min). MS: m/e=384.1 [M+H+].

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography (silica gel/methanol/dichloromethane)
  5. customwas evaporated
  6. dissolutionthe residue was dissolved in a mixture of dichloromethane (0.5 ml) and trifluoroacetic acid (0.5 ml)
  7. customthe volatiles were evaporated

Sources & evidence

ORD record
ord-63b5cf5328634fc6ac2bbca0d5b10ad9
Source dataset
uspto-grants-2011_08
Patent number
US07989657B2

Reaction notes

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