Hydrochloric Acid → 1-t-Butyloxycarbonyl-4-((2-carboxymethoxyphenyl)amino)piperidine

HRID 967409Notes

Reaction equation

HRID 967409 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][C:23]([O:25]CC)=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22914679HCID 22914679, compound

Product 1

HCID 223807041-t-Butyloxycarbonyl-4-((2-carboxymethoxyphenyl)amino)piperidineYield 101%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-(2-Ethoxycarbonylmethoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (21.4 g, 56.5 mmol) was set stirring in MeOH (150 mL). A solution of NaOH (4.5 g, 112.5 mmol) in water (150 mL) was added. After 3 h the mixture was acidified to pH 4 with 6 N HCl. MeOH was removed under reduced pressure and the aqueous layer extracted with EtOAc (2×150 mL). The organics were combined, dried (MgSO4) and evaporated to give 20 g (100%) of a brown solid. MS (electrospray): exact mass calculated for C18H26N2O5, 350.18. m/z found, 351.2 [M+H]+.

Workup

  1. customMeOH was removed under reduced pressure
  2. extractionthe aqueous layer extracted with EtOAc (2×150 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-ba601f4342264542bfacd0069e402636
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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