Hydrochloric Acid → HCID 9895242, compound

HRID 2193907Notes

Reaction equation

HRID 2193907 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:8][C:9]=1[N:10]([C:27](=[O:36])[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[Cl:35])[CH2:11][C:12]1[O:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)=[CH:15][CH:16]=1)=[O:4].[OH-].[Li+].Cl>C1COCC1.O>[Cl:35][C:29]1[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=1[C:27]([N:10]([CH2:11][C:12]1[O:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:25])[F:26])[CH:18]=2)=[CH:15][CH:16]=1)[C:9]1[CH:8]=[C:7]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2])=[O:36]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67299348HCID 67299348, compound

Product 1

HCID 9895242HCID 9895242, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-{(2,4-Dichloro-benzoyl)-[5-(3-trifluoromethyl-phenyl)-furan-2-ylmethyl]-amino}-5-phenyl-thiophene-2-carboxylic acid methyl ester (62 mg, 0.098 mmol) was dissolved in THF (5 mL) and water (2 mL). A solution of lithium hydroxide (13 mg, 3 eq. in 2 mL of water) was added dropwise. After first few drop, a pink color appeared and disappeared. Mixture was stirred for 5 hrs and acidified with 1N HCl-solution. The product was extracted into ethyl acetate, washed once with water, dried over magnesium sulfate. Solvent was evaporated and the residue was purified on silica gel (Bond-Elute 2 g). The product was elute with a 20 mL gradient of Hexane:EtOAc 9:1. 4:1, 7:3, 3:2, 1:1, 2:3 and EtOAc to give the desired product in 76% yield (46 mg).

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. washwashed once with water
  3. dry with materialdried over magnesium sulfate
  4. customSolvent was evaporated
  5. customthe residue was purified on silica gel (Bond-Elute 2 g)
  6. washThe product was elute with a 20 mL gradient of Hexane:EtOAc 9:1

Sources & evidence

ORD record
ord-fdf2c032d7564e549b5b2e4c4f0dcc25
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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