Hydrochloric Acid → HCID 23132796, compound

HRID 2075507Notes

Reaction equation

HRID 2075507 reaction equation
C[O:2][C:3](=[O:32])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH:21]([C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1)[CH3:22])=[O:9])([CH3:6])[CH3:5].Cl>CO.[OH-].[Na+]>[S:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=[C:23]1[CH:21]([O:20][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][C:10]=1[C:8]([NH:7][C:4]([CH3:5])([CH3:6])[C:3]([OH:32])=[O:2])=[O:9])[CH3:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 667012172-{[1-(1-Benzothiazol-2-yl-ethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester

Product 1

HCID 23132796HCID 23132796, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

135 mg 2-{[1-(1-Benzothiazol-2-yl-ethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester in 1 ml methanol and 1.5 ml 1M aqueous sodium hydroxide solution were heated to 100° C. for 2 min in a microwave reactor. The reaction mixture was then acidified using 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulphate, filtrated and concentrated in vacuo. Precipitation with pentane yielded 44 mg of 2-{[1-(1-Benzothiazol-2-yl-ethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid as a colorless solid.

Workup

  1. extractionextracted with ethyl acetate twice
  2. dry with materialThe combined organic layers were dried over magnesium sulphate
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo
  5. customPrecipitation with pentane

Sources & evidence

ORD record
ord-02db5ff206774291a68a66d154b0d29e
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

Loading…