Triethylamine → 4-[[(N-(2-amino-5-chlorobenzoyl)glycyl)amino]methyl]-1-(tert-butoxycarbonyl)piperidine

HRID 133606Notes

Reaction equation

HRID 133606 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:10]=1[C:11]([OH:13])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:40][CH2:41][C:42]([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:43].[OH-].[Na+]>C(Cl)(Cl)Cl>[NH2:8][C:9]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:10]=1[C:11]([NH:40][CH2:41][C:42]([NH:44][CH2:45][CH:46]1[CH2:47][CH2:48][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:50][CH2:51]1)=[O:43])=[O:13]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 124762-Amino-5-chlorobenzoic acidHCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11701760tert-Butyl 4-((2-aminoacetamido)methyl)piperidine-1-carboxylate

Product 1

HCID 184261834-[[(N-(2-amino-5-chlorobenzoyl)glycyl)amino]methyl]-1-(tert-butoxycarbonyl)piperidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (0.75 mL, 5.4 mmol), 2-amino-5-chlorobenzoic acid (840 mg, 4.9 mmol), EDCI (940 mg, 4.9 mmol) and HOBt (660 mg, 4.9 mmol) were added to a chloroform (25 mL) solution of 4-[(glycylamino)methyl]-1-(tert-butoxycarbonyl)piperidine (1.33 g, 4.90 mmol). The resulting mixture was stirred at room temperature for 3 hours, and a 2 M aqueous solution of NaOH (20 mL) was then added to the mixture. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (20 mL×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 thereby provide 4-[[(N-(2-amino-5-chlorobenzoyl) glycyl)amino]methyl]-1-(tert-butoxycarbonyl)piperidine as a solid (1.63 g, 78%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (20 mL×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) to thereby provide 4-[[(N-(2-amino-5-chlorobenzoyl) glycyl)amino]methyl]-1-(tert-butoxycarbonyl)piperidine as a solid (1.63 g, 78%)

Sources & evidence

ORD record
ord-ed77b9e6f82d4f3eb1bb612efdacf7c4
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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