Hydrochloric Acid → HCID 66671769, compound

HRID 446616Notes

Reaction equation

HRID 446616 reaction equation
[Cl:1][C:2]1[C:3]([N:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])[CH3:18])=[CH:4][C:5]([O:15][CH3:16])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[OH-].[Na+].Cl.C(OCC)(=O)C>C(O)C>[C:10]([O:9][C:7]([C:6]1[C:5]([O:15][CH3:16])=[CH:4][C:3]([N:17]([CH3:18])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[C:2]([Cl:1])[CH:14]=1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86663481HCID 86663481, compound

Product 1

HCID 66671769HCID 66671769, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (200 mg, 0.48 mmol) obtained in Example 99c was dissolved in ethanol (4 mL), a 1 N aqueous sodium hydroxide solution (1.00 mL, 1.00 mmol) was added, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, a 1 N aqueous hydrochloric acid solution (1.00 mL, 1.00 mmol) was added to the reaction mixture under ice cooling, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give crude 6-{[4-(tert-butoxycarbonyl)-2-chloro-5-methoxyphenyl](methyl)amino}hexanoic acid (189 mg).

Workup

  1. customto separate the layers
  2. customThe resulting organic layer was separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4550490f5b5a4378abdcb2e1fbfd0b0f
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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