Hydrochloric Acid → 5-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]-propionyl}methylamino)pentanoic acid

HRID 1055318Notes

Reaction equation

HRID 1055318 reaction equation
COC(=O)CCCCN([C:10](=[O:35])[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([O:19][C:20](=[O:34])[NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:15][CH2:14]1)C.[Li+].[OH-:38].Cl.[C:40]([OH:44])([CH3:43])(C)C>O>[C:23]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:20]([O:19][CH:16]1[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][C:10]([CH2:14][NH:13][CH2:12][CH2:11][CH2:10][CH2:43][C:40]([OH:44])=[O:38])=[O:35])[CH2:18][CH2:17]1)=[O:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6386tert-Butanol2×HCID 667700995-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}-methylamino)pentanoic acid methyl ester

Product 1

HCID 667818015-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]-propionyl}methylamino)pentanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 5-({3-[4-(biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}-methylamino)pentanoic acid methyl ester (10.21 g, 20.60 mmol), tert-butyl alcohol (20 mL) and water (20 mL) was added a 1:1 mixture of LiOH:water (1.97 g, 41.2 mmol). The resulting mixture was stirred at room temperature for 4 h and then the pH of the mixture was adjusted to about pH 2 using aqueous hydrochloric acid (1 N). The aqueous layer was extracted with DCM (2ט80 mL) and the organic layers were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (12.23 g, quantitative) as an off-white foamy solid (containing residual tert-butyl alcohol).

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted with DCM (2ט80 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give

Sources & evidence

ORD record
ord-082a271bd90049b2a54dae96be589560
Source dataset
uspto-grants-2016_07
Patent number
US09394275B2

Reaction notes

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