4-Methylmorpholine → HCID 178454260, compound

HRID 2260160Notes

Reaction equation

HRID 2260160 reaction equation
ClC(OCC(C)C)=O.[C:9]([NH:19][CH2:20][C:21]([OH:23])=O)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].CN1CCOCC1.[NH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]=[C:39]([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44]>O1CCCC1>[CH3:53][C:51]([CH3:54])([O:50][C:49]([NH:48][C:39]([NH:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][NH:31][C:21](=[O:23])[CH2:20][NH:19][C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])=[N:40][C:41]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:47])=[O:55])[CH3:52]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14349BenzyloxycarbonylglycineHCID 62365Isobutyl chloroformateHCID 10522403HCID 10522403, compound

Product 1

HCID 178454260HCID 178454260, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 1.6 g (14×10-3 mol) of isobutyl chloroformate in 5 ml of tetrahydrofuran is added dropwise to a solution, cooled to -30° C., of 3 g (14×10-3 mol) of carbobenzyloxyglycine and 2.8 g (28×10-3 mol) of N-methylmorpholine in 50 ml of tetrahydrofuran. The reaction medium is stirred for 0.5 hour and a solution of 5.4 g (14×10-3 mol) of bis(1,1-dimethylethyl) [[(6-aminohexyl)imino]methylene]biscarbamate in 20 ml of tetrahydrofuran is added. Stirring is continued for 2 hours at -30° C. and then for 24 hours at room temperature. After filtration of the reaction medium and evaporation of the filtrate under reduced pressure, the residue obtained is purified by chromatography on silica using an ethyl acetate/methylcyclohexane mixture (1/1 v/v) as the eluent to give 7.16 g (yield: 91%) of the expected product in the form of an oil.

Workup

  1. stirringStirring
  2. waitis continued for 2 hours at -30° C.
  3. waitfor 24 hours at room temperature
  4. filtrationAfter filtration of the reaction medium and evaporation of the filtrate under reduced pressure
  5. customthe residue obtained
  6. customis purified by chromatography on silica using an ethyl acetate/methylcyclohexane mixture (1/1 v/v) as the eluent

Sources & evidence

ORD record
ord-ec8476dcaf3a4461b8ee8ae0551ca1b6
Source dataset
uspto-grants-1995_12
Patent number
US05476870

Reaction notes

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