Acetic Acid → HCID 67166102, compound

HRID 553291Notes

Reaction equation

HRID 553291 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:29])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]3[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21]3)[CH:14]=2)=[CH:9][CH:8]=1.C(O)(=O)C>O.O1CCCC1>[CH2:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:28][N:20]1[CH2:19][C:15]1[CH:14]=[C:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C:5]([OH:29])=[O:4])=[CH:12][CH:11]=2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 67165602HCID 67165602, compound

Product 1

HCID 67166102HCID 67166102, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (126 mg) in water (5 mL) was added to a solution of [3′-(1,3-dihydro-iso-indol-2-ylmethyl)-biphenyl-4-yl]-acetic acid methyl ester (0.47 g) in tetrahydrofuran (10 mL) and stirred at room temperature for 72 hour. The reaction mixture was acidified with glacial acetic acid and evaporated. The residue was partitioned between ethyl acetate (20 mL) and water (20 mL). The aqueous was separated and extracted with ethyl acetate (2×20 mL). The combined organics were washed with brine (20 mL), dried (sodium sulfate) and evaporated to give a the subtitle compound as a brown oil (450 mg).

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate (20 mL) and water (20 mL)
  3. customThe aqueous was separated
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. washThe combined organics were washed with brine (20 mL)
  6. dry with materialdried (sodium sulfate)
  7. customevaporated

Sources & evidence

ORD record
ord-e2c88c591f7d4036a7a45010542c6dc0
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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