4-Methylmorpholine → HCID 54050166, compound

HRID 437129Notes

Reaction equation

HRID 437129 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=O)=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH2:36]([O:38][C:39](=[O:43])[N:40]([CH3:42])[NH2:41])[CH3:37]>O1CCCC1.C(Cl)(Cl)Cl>[CH2:36]([O:38][C:39](=[O:43])[N:40]([CH3:42])[NH:41][C:15](=[O:17])[C@@H:14]1[CH2:18][CH2:19][CH2:20][N:13]1[C:11](=[O:12])[C@H:9]([CH3:10])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:37]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 11217246N-methylethoxycarbohydrazideHCID 11902919Boc-ala-pro-OH

Product 1

HCID 54050166HCID 54050166, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 0.16 mole of t-butoxycarbonylalanylproline in 80 ml of dry tetrahydrofuran which has been cooled to -20° to -30° is added 2 ml of N-methylmorpholine and then 2.1 ml of isobutylchloroformate. After stirring for 10 minutes, 0.16 mole of 2-azaalanine ethyl ester and 60 ml of chloroform are added. The reaction mixture is allowed to warm to room temperature overnight, concentrated in vacuo, taken up in ethyl acetate and the insoluble material removed by filtration. Concentration of the filtrate in vacuo gives t-butoxycarbonylalanylprolyl-2-azaalanine ethyl ester.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe insoluble material removed by filtration

Sources & evidence

ORD record
ord-cdf07bab250249fb945d48ca9defdeb9
Source dataset
uspto-grants-1977_06
Patent number
US04029772

Reaction notes

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