4-Methylmorpholine → HCID 45142042, compound

HRID 1441984Notes

Reaction equation

HRID 1441984 reaction equation
CN1CCOCC1.ClC(OCC)=O.[CH2:14]([O:21][C:22]([NH:24][C@H:25]([C:37](O)=[O:38])[CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.O>[C:33]([O:32][C:30]([NH:29][CH2:28][CH2:27][CH2:26][C@H:25]([NH:24][C:22](=[O:23])[O:21][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:37][OH:38])=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 7350734Z-Ndelta-Boc-L-ornithineHCID 21226445Aluminium lithium hydride

Product 1

HCID 45142042HCID 45142042, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

157 mg (1.56 mmol) of 4-methylmorpholine and 169 mg (1.56 mmol) of ethyl chloroformate are added to a solution of 570 mg (1.56 mmol) of N2-[(benzyloxy)carbonyl]-N5-(tert-butoxycarbonyl)-L-ornithine in 10 ml of tetrahydrofuran at −10° C., and the mixture is stirred for 30 min. At this temperature, 3.11 ml (3.11 mmol) of a 1M solution of lithium aluminium hydride in tetrahydrofuran are slowly added dropwise. The mixture is slowly warmed to RT and stirred at RT for 12 h. While cooling in ice, 0.2 ml of water and 0.3 ml of a 4.5% sodium hydroxide solution are cautiously added, and stirring is continued at RT for 3 h. The mixture is filtered and the filtrate is concentrated in vacuo. The residue is dissolved in ethyl acetate, washed with water, dried over magnesium sulfate and again evaporated to dryness in vacuo. The product is reacted without further purification.

Workup

  1. stirringstirred at RT for 12 h
  2. temperatureWhile cooling in ice
  3. stirringstirring
  4. waitis continued at RT for 3 h
  5. filtrationThe mixture is filtered
  6. concentrationthe filtrate is concentrated in vacuo
  7. dissolutionThe residue is dissolved in ethyl acetate
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. customagain evaporated to dryness in vacuo
  11. customThe product is reacted without further purification

Sources & evidence

ORD record
ord-e51e84d146994c80b7d7ae804f9961f2
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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