Hydrochloric Acid → HCID 23132796, compound

HRID 2062075Notes

Reaction equation

HRID 2062075 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 1 M 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-0570a7c5b97343b2a5bfc71789064329
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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