Diisopropylethylamine → N-[[1-[[[4-[(Dimethylamino)methyl]phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methionine methyl ester

HRID 73876Notes

Reaction equation

HRID 73876 reaction equation
C(N(C(C)C)CC)(C)C.Cl.[CH3:11][O:12][C:13](=[O:20])[C@H:14]([CH2:16][CH2:17][S:18][CH3:19])[NH2:15].[CH3:21][N:22]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[O:35][C:34](=[O:36])[C:33]3([CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[N:32]=2)=[CH:27][CH:26]=1)[CH3:23]>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13](=[O:20])[C@H:14]([CH2:16][CH2:17][S:18][CH3:19])[NH:15][C:34]([C:33]1([NH:32][C:31]([C:28]2[CH:29]=[CH:30][C:25]([CH2:24][N:22]([CH3:23])[CH3:21])=[CH:26][CH:27]=2)=[O:35])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)=[O:36]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 576729082-[4-[(Dimethylamino)methyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

Product 1

HCID 24739313N-[[1-[[[4-[(Dimethylamino)methyl]phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methionine methyl esterYield 59.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

129 mg (1 mmol) of diisopropylethylamine was added to a suspension of 84 mg (0.42 mmol) of L-methionine methyl ester hydrochloride and 100 mg (0.35 mmol) of 2-[4-[(dimethylamino)methyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one in 3 ml of toluene, and the mixture was heated under reflux overnight. After the solvent was distilled off under reduced pressure, ethyl acetate was added thereto, and the mixture was washed with saturated brine, followed by drying with sodium sulfate. After the solvent was distilled off under reduced pressure, diethyl ether was added thereto, and the mixture was stirred overnight. The precipitated solid was collected by filtration and dried under reduced pressure to obtain 93 mg (59%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. distillationAfter the solvent was distilled off under reduced pressure, ethyl acetate
  4. additionwas added
  5. washthe mixture was washed with saturated brine
  6. dry with materialby drying with sodium sulfate
  7. distillationAfter the solvent was distilled off under reduced pressure, diethyl ether
  8. additionwas added
  9. filtrationThe precipitated solid was collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-6f56b63e7c3545faaaa3400630012d5e
Source dataset
uspto-grants-2014_09
Patent number
US08829209B2

Reaction notes

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