Hydrochloric Acid → 4-({[(Benzyloxy)carbonyl]amino}methyl)-1-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

HRID 216068Notes

Reaction equation

HRID 216068 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:26]([O:28]C)=[O:27])[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:26]([OH:28])=[O:27])[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 689923421-Tert-butyl 4-methyl 4-((benzyloxycarbonylamino)methyl)piperidine-1,4-dicarboxylate

Product 1

HCID 670368724-({[(Benzyloxy)carbonyl]amino}methyl)-1-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-tert-butyl 4-methyl 4-((benzyloxycarbonylamino)methyl)piperidine-1,4-dicarboxylate from step A in methanol (5 mL) was added 1 N aq. NaOH (0.615 mL, 0.615 mmol). The reaction was heated at 50° C. overnight, acidified to pH 5 with 1 N aq. HCl, and extracted 3× with CH2Cl2. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under vacuum to give the title compound, which was carried on crude. MS (ES+) [M+H]+=393.

Workup

  1. extractionextracted 3× with CH2Cl2
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ac12bec858554a3d9fc4fa2ddd872b49
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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