Sodium Hydroxide → HCID 178524091, compound

HRID 521059Notes

Reaction equation

HRID 521059 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:31]=[CH:30][C:10]2[C@@H:11]3[C@H:16]([CH2:17][CH2:18][C:9]=2[CH:8]=1)[N:15]([C:19]([C:21]1[CH:29]=[CH:28][C:24]2[NH:25][CH:26]=[N:27][C:23]=2[CH:22]=1)=[O:20])[CH2:14][CH2:13][CH2:12]3)=[O:6]>O1CCCC1>[NH:25]1[C:24]2[CH:28]=[CH:29][C:21]([C:19]([N:15]3[C@@H:16]4[C@@H:11]([C:10]5[CH:30]=[CH:31][C:7]([C:5]([OH:6])=[O:4])=[CH:8][C:9]=5[CH2:18][CH2:17]4)[CH2:12][CH2:13][CH2:14]3)=[O:20])=[CH:22][C:23]=2[N:27]=[CH:26]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178497109HCID 178497109, compound

Product 1

HCID 178524091HCID 178524091, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 M aqueous NaOH solution (15 mL) is added to a solution of cis-4-(1H-benzoimidazole-5-carbonyl)-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline-8-carboxylic acid methyl ester (1.60 g) in tetrahydrofuran (15 mL) at room temperature. The resulting solution is stirred at room temperature for 5 h. The solution is concentrated under reduced pressure and water (100 mL) is added to the residue. 1 M Aqueous hydrochloric acid (15 mL) is then added and the precipitate formed is separated by filtration. The precipitate is washed with water and diethyl ether and dried to afford the title compound as a solid. Yield: 1.24 g (80% of theory); LC (method 1): tR=2.09 min; Mass spectrum (ESI+): m/z=376 [M+H]+.

Workup

  1. concentrationThe solution is concentrated under reduced pressure and water (100 mL)
  2. additionis added to the residue
  3. addition1 M Aqueous hydrochloric acid (15 mL) is then added
  4. customthe precipitate formed
  5. customis separated by filtration
  6. washThe precipitate is washed with water and diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-76a8d45f393e46fe8d88843cc61d0305
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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