4-Methylmorpholine → HCID 54170884, compound

HRID 437131Notes

Reaction equation

HRID 437131 reaction equation
[C:1]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.FC(F)(F)C(O)=O.[CH2:39]([O:41][C:42](=[O:58])[N:43]([CH3:57])[NH:44][C:45](=[O:56])[C@@H:46]1[CH2:50][CH2:49][CH2:48][N:47]1[C:51](=[O:55])[C@H:52]([CH3:54])[NH2:53])[CH3:40]>O1CCCC1.C(Cl)(Cl)Cl>[CH2:39]([O:41][C:42](=[O:58])[N:43]([CH3:57])[NH:44][C:45](=[O:56])[C@@H:46]1[CH2:50][CH2:49][CH2:48][N:47]1[C:51](=[O:55])[C@H:52]([CH3:54])[NH:53][C:14](=[O:16])[C@H:12]([CH3:13])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH3:40]

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 736104N-carbobenzyloxyalanineHCID 68125460HCID 68125460, compound

Product 1

HCID 54170884HCID 54170884, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.005 mole of carbobenzyloxyalanine in 100 ml of dry tetrahydrofuran which has been cooled to -20° to -30° is added 1 ml of N-methylmorpholine and then 1 ml of isobutyl-chloroformate. After stirring for 10 minutes there is added 0.005 mole of alanylprolyl-2-azaalanine ethyl ester trifluoroacetic acid salt, 60 ml of chloroform and 1 ml of N-methylmorpholine. The reaction mixture is stirred overnight at room temperature, concentrated in vacuo, the residue treated with ethylacetate and the insoluble material removed by filtration. The filtrate is concentrated in vacuo and the residue chromatographed on a silica gel. Elution with ethyl acetate gives carbobenzyloxyalanylalanylprolyl-2-azaalanine ethyl ester.

Workup

  1. stirringThe reaction mixture is stirred overnight at room temperature
  2. concentrationconcentrated in vacuo
  3. additionthe residue treated with ethylacetate
  4. customthe insoluble material removed by filtration
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe residue chromatographed on a silica gel
  7. washElution with ethyl acetate

Sources & evidence

ORD record
ord-56733b071fa74516bc965fee20d5e578
Source dataset
uspto-grants-1977_06
Patent number
US04029772

Reaction notes

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