Hydrochloric Acid → 2-[(S)-3-tert-Butoxycarbonyl-1-(4-ethoxycarbonyl-piperazine-1-carbonyl)-propylcarbamoyl]-quinoline-4-carboxylic acid

HRID 1185441Notes

Reaction equation

HRID 1185441 reaction equation
C([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16](=[O:41])[NH:17][C@H:18]([C:28]([N:30]2[CH2:35][CH2:34][N:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]2)=[O:29])[CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>C1COCC1>[C:24]([O:23][C:21]([CH2:20][CH2:19][C@H:18]([NH:17][C:16]([C:8]1[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:41])[C:28]([N:30]1[CH2:31][CH2:32][N:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:34][CH2:35]1)=[O:29])=[O:22])([CH3:25])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 685997922-[(S)-3-tert-Butoxycarbonyl-1-(4-ethoxycarbonyl-piperazine-1-carbonyl)-propylcarbamoyl]-quinoline-4-carboxylic acid ethyl ester

Product 1

HCID 685995742-[(S)-3-tert-Butoxycarbonyl-1-(4-ethoxycarbonyl-piperazine-1-carbonyl)-propylcarbamoyl]-quinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.1 g of 2-[(S)-3-tert-Butoxycarbonyl-1-(4-ethoxycarbonyl-piperazine-1-carbonyl)-propylcarbamoyl]-quinoline-4-carboxylic acid ethyl ester in 10 ml of THF, 2 ml of a 1 M aqueous NaOH solution was added. After stirring for 5 h at RT additional 1 ml of a 1 M aqueous NaOH solution was added and allowed to stir upon completion of the reaction. Then, the reaction was acidified to pH 1 with diluted aqueous hydrochloric acid and extracted with DCM (3×100 ml). The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was used in the next reaction step without further purification. Yield: 1.0 g.

Workup

  1. additionwas added
  2. extractionextracted with DCM (3×100 ml)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customThe crude product was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-d7a7b3b9ee7d4e2cb77e365152008ed0
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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