Dicyclohexylcarbodiimide → HCID 178451977, compound

HRID 2110045Notes

Reaction equation

HRID 2110045 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:25][C:26](=[O:28])[NH2:27])=S)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][C:26](=[O:28])[N:27]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 866105084-{[({[2-(Carbamoylmethyl)phenyl]amino}thioxomethyl)amino]methyl}piperidine carboxylic acid tert-butyl ester

Product 1

HCID 178451977HCID 178451977, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 4-{[({[2-(carbamoylmethyl)phenyl]amino}thioxomethyl)amino]methyl}piperidine carboxylic acid tert-butyl ester (410 mg, 1.01 mmol) in tetrahydrofuran (15 mL), N,N′-dicyclohexylcarbodiimide (208 mg, 1.01 mmol) was added and the mixture was stirred at room temperature for 6 hours. The filtrate obtained by filtering the insoluble portion was concentrated under reduced pressure, and the concentrate was suspended in a solution of n-hexane:ethyl acetate=1:2 (3 mL). The insoluble portion was refiltered, and the residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/3→1/2) to obtain the title compound. Yield: 193 mg (51%).

Workup

  1. additionwas added
  2. customThe filtrate obtained
  3. filtrationby filtering the insoluble portion
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue obtained
  6. concentrationby concentrating the filtrate under reduced pressure
  7. customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=2/3→1/2)

Sources & evidence

ORD record
ord-556b656159634713b233fc941b49f201
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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