Triethylamine → HCID 66873110, compound

HRID 2406015Notes

Reaction equation

HRID 2406015 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:22][NH2:23])([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1.[OH-].[Na+]>ClCCl.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH2:22][NH:23][C:36](=[O:37])[C:35]2[CH:39]=[CH:40][C:32]([Cl:31])=[CH:33][CH:34]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 14798Sodium HydroxideHCID 45139441HCID 45139441, compound

Product 1

HCID 66873110HCID 66873110, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-aminomethyl-4-tert-butoxycarbonylamino-piperidine-1-carboxylic acid tert-butyl ester (12.2 mg, 0.037 mmol) and triethylamine (16 μL, 0.12 mmol) in dry dichloromethane (4 mL) was added 4-chlorobenzoyl chloride (5 μL, 0.037 mmol). After stirring for 18 hours at room temperature, the reaction mixture was partionated between dichloromethane (2 mL) and water (1 mL) with 10% aqueous sodium hydroxide (0.1 mL). The two layers were separated and the aqueous phase was further extracted with dichloromethane (2 mL). The combined organic layers were dried (Mg2SO4), filtered and concentrated. Preparative TLC, eluting with 10% methanol-dichloromethane, gave 4-tert-butoxycarbonylamino-4-[(4-chloro-benzoylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (6 mg, 0.013 mmol, 35%). LC-MS (LCT2) m/z 490 [M+Na+], Rt 8.20 min.

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous phase was further extracted with dichloromethane (2 mL)
  3. dry with materialThe combined organic layers were dried (Mg2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washPreparative TLC, eluting with 10% methanol-dichloromethane

Sources & evidence

ORD record
ord-cb9d01b1b3bd4fe2a398dfd2ffb9d538
Source dataset
uspto-grants-2014_08
Patent number
US08809336B2

Reaction notes

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