4-Methylmorpholine → HCID 70566312, Verbindung

HRID 1680570

Reaktionsgleichung

Reaktionsgleichung von HRID 1680570
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[NH2:36][C:37]12[CH2:46][CH:41]3[CH2:42][CH:43]([CH2:45][C:39]([C:47]([O:49][CH3:50])=[O:48])([CH2:40]3)[CH2:38]1)[CH2:44]2.NC12CC3CC(CC(C(OC)=O)(C3)C1)C2>CN(C)C=O.O>[C:1]([NH:8][C@H:9]([C:17]([CH:38]1[C:37]2([NH2:36])[CH2:44][CH:43]3[CH2:42][CH:41]([CH2:40][C:39]1([C:47]([O:49][CH3:50])=[O:48])[CH2:45]3)[CH2:46]2)=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Komponenten

8

Edukt 5

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 2852886Methyl 3-aminoadamantane-1-carboxylate hydrochlorideHCID 2852887Methyl 3-aminoadamantane-1-carboxylate

Produkt 1

HCID 70566312HCID 70566312, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

5.09 Grams of Boc-L-phenylalanine is dissolved in 25 ml of dry dimethylformamide and 2.13 ml of N-methylmorpholine is added. The reaction mixture is cooled to -50° C. and 2.51 ml of isobutylchloroformate is added. The reaction mixture is stirred for 15 minutes, then 1.77 ml of N-methylmorpholine and 3.93 g of methyl 3-amino-1-adamantanecarboxylate hydrochloride are added and the reaction mixture is stirred until all the methyl 3-amino-1-adamantanecarboxylate dissolves then stored for 3 days at 5° C. The reaction mixture is poured into 100 ml of water and extracted twice with 50 ml of ethyl acetate. The ethyl acetate fractions are washed twice with 50 ml of water, 50 ml of a 0.5 solution of potassium bisulfate, 50 ml of water, 50 ml of a 0.5 M solution of potassium bicarbonate, and 50 ml of water then dried over magnesium sulfate. The solvent is removed under reduced pressure, and the residue is dissolved in 150 ml of 10% chloroform in hexane and purified by low pressure chromatography on silica gel using a gradient of 10% to 50% solution of chloroform in hexane as eluent. Removal of the solvent under vacuum gives the product methyl Boc-L-phenylalanyl-3-amino-1-adamantanecarboxylate which is represented by the following formula ##STR23##

Aufarbeitung

  1. dissolutiondissolves
  2. waitthen stored for 3 days at 5° C
  3. extractionextracted twice with 50 ml of ethyl acetate
  4. washThe ethyl acetate fractions are washed twice with 50 ml of water, 50 ml of a 0.5 solution of potassium bisulfate, 50 ml of water, 50 ml of a 0.5 M solution of potassium bicarbonate, and 50 ml of water
  5. dry with materialthen dried over magnesium sulfate
  6. customThe solvent is removed under reduced pressure
  7. dissolutionthe residue is dissolved in 150 ml of 10% chloroform in hexane
  8. custompurified by low pressure chromatography on silica gel using a gradient of 10% to 50% solution of chloroform in hexane as eluent
  9. customRemoval of the solvent under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b3e7dd5d90ae4a6aa08835b747db4187
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04273704

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