Water → EthanediaMide iMpurity D

HRID 2361001Notes

Reaction equation

HRID 2361001 reaction equation
C([N:3]([CH2:6]C)CC)C.[C:8]([OH:13])(=O)[C:9](O)=[O:10].[NH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH2:17][C@H:16]1[NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].[ClH:34].O=[CH:36][C:37](O)=O.O.[C:41](#[N:43])[CH3:42]>>[C:29]([O:28][C:27](=[O:33])[NH:26][C@@H:16]1[CH2:17][C@@H:18]([C:21]([N:23]([CH3:24])[CH3:25])=[O:22])[CH2:19][CH2:20][C@@H:15]1[NH:14][C:8](=[O:13])[C:9]([NH:43][C:41]1[CH:42]=[CH:36][C:37]([Cl:34])=[CH:6][N:3]=1)=[O:10])([CH3:30])([CH3:32])[CH3:31]

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 8471TriethylamineHCID 15620608HCID 15620608, compoundHCID 46913548tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate oxalate

Product 1

HCID 46911214EthanediaMide iMpurity D

Procedure

Triethylamine (169 mL) was added at 60° C. to a suspension (550 mL) of t-butyl {(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl}carbamate oxalate (100.1 g) in acetonitrile. At the same temperature, ethyl[5-chloropyridin-2-yl]amino](oxo)acetate hydrochloride (84.2 g) was added to the mixture, followed by stirring for 6 hours. Thereafter, the mixture was stirred at room temperature for 16 hours. Water was added to the reaction mixture, followed by stirring at 10° C. for 1.5 hours. The formed crystals were recovered by filtration, to thereby yield 106.6 g of the title compound.

Workup

  1. stirringThereafter, the mixture was stirred at room temperature for 16 hours
  2. stirringby stirring at 10° C. for 1.5 hours
  3. filtrationThe formed crystals were recovered by filtration

Sources & evidence

ORD record
ord-a8a0a1c7bd4642a2bd47362993be1bce
Source dataset
uspto-grants-2014_04
Patent number
US08686189B2

Reaction notes

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