Hydrochloric Acid → HCID 68777040, compound

HRID 1253907Notes

Reaction equation

HRID 1253907 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:15]=1[CH2:14][N:13]([C:16](=[O:37])[CH2:17][CH:18]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])[CH2:12][C:11]1[CH:38]=[CH:39][CH:40]=[CH:41][C:10]2=1)=[O:5])C.[OH-].[Li+].Cl>C1COCC1.O>[C:33]([O:32][C:30]([NH:29][CH:18]([CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])[CH2:17][C:16]([N:13]1[CH2:14][C:15]2[N:9]([CH:8]=[N:7][C:6]=2[C:4]([OH:5])=[O:3])[C:10]2[CH:41]=[CH:40][CH:39]=[CH:38][C:11]=2[CH2:12]1)=[O:37])=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68775916HCID 68775916, compound

Product 1

HCID 68777040HCID 68777040, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl ester (100 mg, 0.17 mmol) in THF (5 mL) and water (5 mL), was added lithium hydroxide (43 mg, 1.03 mmol). The reaction mixture was stirred at r.t. overnight. After the completion of the reaction as confirmed by TLC, the reaction mixture was cooled to 0° C. and neutralized with 10% HCl solution to pH˜4. The compound was extracted with ethylacetate (15 mL). The organic layer was washed with water, separated, dried over Na2SO4 and concentrated in vacuo to afford 5-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid (85 mg, 89%) as a viscous gel which was used without further purification for the next step.

Workup

  1. customAfter the completion of the reaction
  2. extractionThe compound was extracted with ethylacetate (15 mL)
  3. washThe organic layer was washed with water
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ee99d3edc134d52ba5168e0bfca0ecc
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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