Triethylamine → 4-[{(N-(benzyloxycarbonyl)glycyl)amino}methyl]1-(tert-butoxycarbonyl)piperidine

HRID 133604Notes

Reaction equation

HRID 133604 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][C:16]([NH:18][CH2:19][C:20]([OH:22])=O)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:44][CH2:45][CH:46]1[CH2:51][CH2:50][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:48][CH2:47]1.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:8]([O:15][C:16]([NH:18][CH2:19][C:20]([NH:44][CH2:45][CH:46]1[CH2:51][CH2:50][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:48][CH2:47]1)=[O:22])=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 14349BenzyloxycarbonylglycineHCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 117111694-[{(N-(benzyloxycarbonyl)glycyl)amino}methyl]1-(tert-butoxycarbonyl)piperidineYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (2.8 mL, 20 mmol), N-(benzyloxycarbonyl)glycine (3.77 g, 18 mmol), EDCI (3.45 g, 18 mmol) and HOBt (2.43 g, 18 mmol) were added to a chloroform (80 mL) solution of 4-(aminomethyl)-1-(tert-butoxycarbonyl)piperidine (3.54 g, 16.5 mmol). The resulting mixture was stirred at room temperature for 15 hours, and a 2 M aqueous solution of NaOH (100 mL) was then added to the mixture. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (100 mLX 3). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The obtained crude product was purified by column chromatography (SiO2, ethyl acetate) to provide 4-[[(N-(benzyloxycarbonyl) glycyl)amino]methyl]-1-(tert-butoxycarbonyl)piperidine as an amorphous solid (6.27 g, 94%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (100 mLX 3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe obtained crude product
  7. customwas purified by column chromatography (SiO2, ethyl acetate)

Sources & evidence

ORD record
ord-8b185a31879a4692ac4a86579f4a24c4
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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