4-Methylmorpholine → HCID 53934336, compound

HRID 461785Notes

Reaction equation

HRID 461785 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:29]([O:36][C:37](=[O:44])[C@H:38]([CH2:40][CH:41]([CH3:43])[CH3:42])[NH2:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1.C(Cl)Cl.O1CCCC1>[CH2:29]([O:36][C:37](=[O:44])[C@H:38]([CH2:40][CH:41]([CH3:42])[CH3:43])[NH:39][C:11](=[O:13])[C@H:9]([CH3:10])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 85082Tert-butoxycarbonylalanineHCID 6451313Benzyl L-leucinate

Product 1

HCID 53934336HCID 53934336, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a solution of N-tert-butoxycarbonylalanine (0.06 mole) and N-methylmorpholine (0.06 mole) in dry tetrahydrofuran (100 ml) at -20° to -25° is added isobutyl chloroformate (0.06 mole) with stirring. After 10-15 minutes, a solution of leucine benzyl ester (0.06 mole) and N-methylmorpholine (6.8 ml) in methylene chloride-tetrahydrofuran (1:1, 100 ml) is added over a period of 1/2 hour. The mixture is allowed to warm to room temperature and stirred at room temperature overnight. The resulting mixture is concentrated in vacuo and the residue extracted between chloroform and dilute hydrochloric acid. The chloroform layer is separated, washed with water, dried over sodium sulfate and concentrated to give the crude N-tert-butoxycarbonylalanylleucine benzyl ester to be used as in the next step.

Workup

  1. stirringstirred at room temperature overnight
  2. concentrationThe resulting mixture is concentrated in vacuo
  3. extractionthe residue extracted between chloroform and dilute hydrochloric acid
  4. customThe chloroform layer is separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fe8ad5f59c5a428f985188f7b2b1e306
Source dataset
uspto-grants-1977_12
Patent number
US04064236

Reaction notes

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