Hydrochloric Acid → HCID 11692572, compound

HRID 2428070Notes

Reaction equation

HRID 2428070 reaction equation
C[O:2][C:3](=[O:42])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:21]=[C:20]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][CH:25]=3)[N:19]=[C:18]([C:32]#[C:33][C:34]3[CH:39]=[CH:38][C:37]([CH2:40][OH:41])=[CH:36][CH:35]=3)[CH:17]=2)=[C:11]2[C:7]=1[CH2:8][CH2:9][CH2:10]2.Cl.O.C(OCC)(=O)C>C1COCC1.C(O)C.[OH-].[Na+]>[OH:31][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]#[C:22][C:20]2[CH:21]=[C:16]([S:15][C:12]3[CH:13]=[CH:14][C:6]([O:5][CH2:4][C:3]([OH:42])=[O:2])=[C:7]4[C:11]=3[CH2:10][CH2:9][CH2:8]4)[CH:17]=[C:18]([C:32]#[C:33][C:34]3[CH:35]=[CH:36][C:37]([CH2:40][OH:41])=[CH:38][CH:39]=3)[N:19]=2)=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 67266406HCID 67266406, compound

Product 1

HCID 11692572HCID 11692572, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

{7-[2,6-Bis-(4-hydroxymethyl-phenylethynyl)-pyridine-4-ylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester (70 mg; 0.12 mmol) was dissolved in a mixture of THF and ethanol (1:2) (30 ml) and 1N sodium hydroxide (1 ml) was added. The reaction mixture was stirred for about 16 h and 1N aqueous hydrogen chloride (2 ml), water (10 ml) and ethyl acetate (20 ml) were added. The organic phase was separated from the aqueous phase and the aqueous phase was extracted with ethyl acetate (10 ml). The pooled organic phases were washed with water (10 ml), dried and evaporated to dryness to give {7-[2,6-bis-(4-hydroxymethyl-phenylethynyl)-pyridin-4-ylsulfanyl]-indan-4-yloxy}-acetic acid. Yield: 64 mg LC-MS (system 1): Rt: 2.09; Mw: 562.5.

Workup

  1. additionwas added
  2. customThe organic phase was separated from the aqueous phase
  3. extractionthe aqueous phase was extracted with ethyl acetate (10 ml)
  4. washThe pooled organic phases were washed with water (10 ml)
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a898e84de1e84207b1679adc4378fff9
Source dataset
uspto-grants-2011_06
Patent number
US07968723B2

Reaction notes

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