Hydrochloric Acid → 1-(3-tert-Butoxycarbonylamino-benzyl)-piperidine-4-carboxylic acid

HRID 1486690Notes

Reaction equation

HRID 1486690 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=2)[CH2:8][CH2:7]1)=[O:5])C.Cl>O.CO>[C:23]([O:22][C:20]([NH:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][N:9]1[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 867065211-(3-tert-Butoxycarbonylamino-benzyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 867065221-(3-tert-Butoxycarbonylamino-benzyl)-piperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-(3-tert-butoxycarbonylamino-benzyl)-piperidine-4-carboxylic acid ethyl ester (7.6 g, 21.4 mmol) in a mixture of water (90 mL) and MeOH (90 mL) at RT is treated at once with LiOH mono hydrate (922 mg, 22 mmol). The mixture is stirred at RT for 18 h then HCl 1N (22 mmol, 22 mL) is added and the reaction mixture is stirred at RT for 30 min. The solvents are removed under reduce pressure and the crude acid is dried under high vacuum. The crude title compound containing LiCl is used for the next step. LC-MS A: tR=0.56 min; [M+H]+=335.26.

Workup

  1. stirringthe reaction mixture is stirred at RT for 30 min
  2. customThe solvents are removed
  3. dry with materialthe crude acid is dried under high vacuum
  4. additionThe crude title compound containing LiCl

Sources & evidence

ORD record
ord-c027aa8d479c4265b08bef0f6ba40ee9
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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