Hydrochloric Acid → 2-({6-[(2-{4-[(Biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}amino)-1,3-thiazole-5-carboxylic acid

HRID 446620Notes

Reaction equation

HRID 446620 reaction equation
[OH-].[Na+].C([C:5]1[N:6]=[C:7]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([N:21]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([O:31][C:32](=[O:46])[NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:27][CH2:26]2)[CH3:22])=[O:20])[S:8][C:9]=1[C:10]([OH:12])=[O:11])C.Cl>C(O)C>[C:35]1([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[NH:33][C:32]([O:31][CH:28]1[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][N:21]([CH3:22])[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:7]2[S:8][C:9]([C:10]([OH:12])=[O:11])=[CH:5][N:6]=2)[CH2:30][CH2:29]1)=[O:46]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86663484Ethyl 2-({6-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}amino)-1,3-thiazole-5-carboxylic acid

Product 1

HCID 866634832-({6-[(2-{4-[(Biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}amino)-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 10 N aqueous sodium hydroxide solution (27 μL) was added to a solution of the compound obtained in Example 104a in ethanol (3.0 mL), and the mixture was stirred at room temperature for 16 hours. The mixture was ice cooled, then a 6 N aqueous hydrochloric acid solution (453 μL, 1) was added, and then the solvent was evaporated under reduced pressure. Methanol (2 mL) and toluene (10 mL) were added to the residue, and the solvent was evaporated under reduced pressure again to give crude 2-({6-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}amino)-1,3-thiazole-5-carboxylic acid (357 mg).

Workup

  1. temperaturecooled
  2. customthe solvent was evaporated under reduced pressure
  3. additionMethanol (2 mL) and toluene (10 mL) were added to the residue
  4. customthe solvent was evaporated under reduced pressure again

Sources & evidence

ORD record
ord-f4372ce8f5b14f4480c4e8439ff6ee3c
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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