HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

4-Methylmorpholine → HCID 178501376, compound

HRID 1395811
Notes
Print preview

Reaction equation

HRID 1395811 reaction equation
[C:1]([O:5][C:6]([N:8]([N+:20]([O-:22])=[O:21])[C@H:9]([C:17]([OH:19])=O)[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:16])[NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.Cl.[CH3:39][O:40][C:41](=[O:59])[C@H:42]([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][CH:53]=1)[NH:43][C:44](=[O:50])[C@H:45]([CH:47]([CH3:49])[CH3:48])[NH2:46]>C(Cl)Cl>[CH3:39][O:40][C:41](=[O:59])[C@H:42]([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][CH:53]=1)[NH:43][C:44](=[O:50])[C@H:45]([CH:47]([CH3:49])[CH3:48])[NH:46][C:17](=[O:19])[C@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:16])[NH2:15])[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[N+:20]([O-:22])=[O:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 14445713Valyltyrosine methyl ester hydrochlorideHCID 178454196HCID 178454196, compound

Product 1

HCID 178501376HCID 178501376, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
-70 °C

Procedure

21.5 g of t-butoxycarbonylnitroarginine is dissolved in 200 ml of methylene chloride. 15.0 ml of N-methylmorpholine is added to the solution. The solution is cooled to -70° C. 8.8 ml of isobutyl chloroformate is then added. The reaction mixture is warmed up to -15° C. and stirred for 5 minutes. The reaction mixture is again cooled to -70° C. 22.3 g of valyltyrosine methyl ester hydrochloride is added to the reaction mixture. The reaction mixture is allowed to warm to room temperature, and then is stirred for 16 hours. The reaction mixture is extracted three times with 0.5 M potassium bisulfate and once with brine. The methylene chloride solution is dried over anhydrous sodium sulfate, filtered and stripped of solvent. The residue is dissolved in 200 ml of ethyl ether. The ether solution is added to cold rapidly stirring Skellysolve B. The white precipitate is filtered and dried to afford the product t-butoxycarbonylnitroarginylvalyltyrosine methyl ester.

Workup

  1. temperatureThe reaction mixture is warmed up to -15° C.
  2. temperatureThe reaction mixture is again cooled to -70° C
  3. temperatureto warm to room temperature
  4. stirringis stirred for 16 hours
  5. extractionThe reaction mixture is extracted three times with 0.5 M potassium bisulfate
  6. dry with materialThe methylene chloride solution is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. dissolutionThe residue is dissolved in 200 ml of ethyl ether
  9. additionThe ether solution is added to cold rapidly stirring Skellysolve B
  10. filtrationThe white precipitate is filtered
  11. customdried

Sources & evidence

ORD record
ord-d78dbb0668664858aefc855b83fa47c9
Source dataset
uspto-grants-1980_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04204991

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes