Hydrochloric Acid → HCID 86651789, compound

HRID 2359804Notes

Reaction equation

HRID 2359804 reaction equation
[C:1]([O:5][C:6](=[O:45])[CH2:7][N:8](C(OC(C)(C)C)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)(=[O:31])=[O:30])[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[S:25][CH:26]=[CH:27][N:28]=3)=[CH:20][CH:19]=2)[N:10]=1)(C)([CH3:3])[CH3:2].Cl.C(=O)([O-])O.[Na+]>C(O)(C)C>[CH:1]([O:5][C:6](=[O:45])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)(=[O:31])=[O:30])[NH:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[S:25][CH:26]=[CH:27][N:28]=3)=[CH:22][CH:23]=2)[N:10]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86651779HCID 86651779, compound

Product 1

HCID 86651789HCID 86651789, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl[tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate (200 mg, 0.307 mmol) obtained in Example 3-(a) in isopropanol (1.5 ml) was added a 4N hydrogen chloride/-1,4-dioxane solution (1.5 ml), followed by stirring at 40° C. for 9 hours. After completion of the reaction, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=1:2 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (132 mg) (pure content: 118 mg) as a colorless oil. (Yield: 80%)

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additioncontaining the desired compound
  6. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-daf439fd92dc4baebc470f9cc07730ff
Source dataset
uspto-grants-2014_04
Patent number
US08685986B2

Reaction notes

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