Hydrochloric Acid → HCID 10201706, compound

HRID 1070414Notes

Reaction equation

HRID 1070414 reaction equation
C[Si](C)(C)CC[O:5][C:6](=[O:33])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[NH:14][C:15]([O:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)=[O:16].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.Cl>CN(C=O)C>[C:24]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:22][C:21]([O:20][CH2:19][CH2:18][O:17][C:15]([NH:14][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([Cl:13])[C:7]=2[C:6]([OH:33])=[O:5])=[O:16])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 69687679HCID 69687679, compound

Product 1

HCID 10201706HCID 10201706, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[2-(biphenyl-4-yloxy)-ethoxycarbonylamino]-6-chloro-benzoic acid 2-trimethylsilanyl-ethyl ester (340 mg, 0.664 mmol) and 1.0M tetrabutyl ammonium fluoride in THF (0.66 mL, 0.6636 mmol) in DMF (6 mL) and the mixture was stirred for 2 h. 2N HCl was added to adjust the pH to 1-2 and the mixture was partitioned between water and ethyl acetate. The combined organics were washed with water, then brine dried over magnesium sulfate and concentrated to dryness. Purification by crystallization gave 0.121 g of 2-[2-(biphenyl-4-yloxy)-ethoxycarbonylamino]-6-chloro-benzoic acid as a white solid, 801, mp:157.5-158.9.

Workup

  1. customthe mixture was partitioned between water and ethyl acetate
  2. washThe combined organics were washed with water
  3. dry with materialbrine dried over magnesium sulfate
  4. concentrationconcentrated to dryness
  5. customPurification
  6. customby crystallization

Sources & evidence

ORD record
ord-d9580272b3ba44b785a66458e1dcb8a8
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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