Dicyclohexylcarbodiimide → HCID 16047845, compound

HRID 570093Notes

Reaction equation

HRID 570093 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[N:3]1[CH2:9][C:10]([NH:12][CH2:13][C:14]([OH:16])=[O:15])=[O:11].O[N:18]1[C:22](=[O:23])[CH2:21][CH2:20][C:19]1=[O:24].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[O:24]=[C:19]1[CH2:20][CH2:21][C:22](=[O:23])[N:18]1[O:15][C:14](=[O:16])[CH2:13][NH:12][C:10](=[O:11])[CH2:9][N:3]1[CH:4]([CH3:8])[CH2:5][CH2:6][CH2:7][CH:2]1[CH3:1]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 59404491N-[(2,6-Dimethylpiperidin-1-yl)acetyl]glycine

Product 1

HCID 16047845HCID 16047845, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.54 g (20 mMol) [2-(2,6-Dimethyl-piperidin-1-yl)acetylamino]-acetic acid (30) were added to 2.30 g (20 mMol) N-Hydroxysuccinimide and 4.12 g (20 mMol) N,N′-Dicyclohexyl-carbodiimide dissolved in 150 ml dichloromethane. The reaction mixture was stirred for 16 h at room temperature. The solution was filtered and the filtrate was evaporated in vacuo to dryness. The residue was dissolved in 50 mL dichloromethane and treated with charcoal. After filtration, the solution was evaporated in vacuo to dryness and the product was recrystallised from ethyl acetate.

Workup

  1. filtrationThe solution was filtered
  2. customthe filtrate was evaporated in vacuo to dryness
  3. dissolutionThe residue was dissolved in 50 mL dichloromethane
  4. additiontreated with charcoal
  5. filtrationAfter filtration
  6. customthe solution was evaporated in vacuo to dryness
  7. customthe product was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-476249cbcfe6473cb8c58188d6000e04
Source dataset
uspto-grants-2015_05
Patent number
US09023656B2

Reaction notes

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