Hydrochloric Acid → HCID 11611928, compound

HRID 491857Notes

Reaction equation

HRID 491857 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Br:15])[CH:13]=2)[N:8]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:7]=1.[OH-].[Li+].C(OCC)(=O)C.Cl>C1COCC1>[Br:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:16]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)(=[O:17])=[O:18])[CH:7]=[C:6]2[O:5][CH2:4][C:3]([OH:27])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 57678938HCID 57678938, compound

Product 1

HCID 11611928HCID 11611928, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

[5-Bromo-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yloxy]-acetic acid methyl ester (22, 32.0 mg, 0.007 mmol) was dissolved in THF (1.50 mL) and 1M lithium hydroxide (0.4 mL) was added to this solution. After stirring for 30 min at 25° C., ethyl acetate was added and the mixture was acidified with 1M hydrochloric acid. The organic layer was dried over magnesium sulfate, filtered and concentrated at reduced pressure to obtain a white solid (23, 28 mg, 90% yield). MS(ESI) [M−H+]−=438.0; 440.0.

Workup

  1. dry with materialThe organic layer was dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated at reduced pressure
  4. customto obtain a white solid (23, 28 mg, 90% yield)

Sources & evidence

ORD record
ord-1c71659753504fc4b668207f75993da5
Source dataset
uspto-grants-2009_05
Patent number
US07531568B2

Reaction notes

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