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Hydrochloric Acid → Pepstatin glutamic acid

HRID 2052465
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2052465
[CH3:1][C@H:2]([NH:17][C:18]([CH2:20][C@H:21]([OH:48])[C@@H:22]([NH:27][C:28]([C@@H:30]([NH:34][C:35]([C@@H:37]([NH:41][C:42]([CH2:44][CH:45]([CH3:47])[CH3:46])=[O:43])[CH:38]([CH3:40])[CH3:39])=[O:36])[CH:31]([CH3:33])[CH3:32])=[O:29])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:19])[C:3]([NH:5][C@H:6]([C@@H:11]([OH:16])[CH2:12][C:13]([OH:15])=[O:14])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4].Cl.[NH2:50][C@H:51]([C:57]([OH:59])=[O:58])[CH2:52][CH2:53][C:54]([OH:56])=[O:55].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>O.C(N(CC)CC)C.CS(C)=O.CN(C)C=O>[CH3:1][C@H:2]([NH:17][C:18]([CH2:20][C@H:21]([OH:48])[C@@H:22]([NH:27][C:28]([C@@H:30]([NH:34][C:35]([C@@H:37]([NH:41][C:42]([CH2:44][CH:45]([CH3:47])[CH3:46])=[O:43])[CH:38]([CH3:40])[CH3:39])=[O:36])[CH:31]([CH3:32])[CH3:33])=[O:29])[CH2:23][CH:24]([CH3:25])[CH3:26])=[O:19])[C:3]([NH:5][C@H:6]([C@@H:11]([OH:16])[CH2:12][C:13]([OH:15])=[O:14])[CH2:7][CH:8]([CH3:9])[CH3:10])=[O:4].[NH2:50][C@H:51]([C:57]([OH:59])=[O:58])[CH2:52][CH2:53][C:54]([OH:56])=[O:55]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 33032L-Glutamic AcidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 5478883Pepstatin

Produkt 1

HCID 86736802Pepstatin glutamic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 679Dimethyl SulfoxideLösungsmittel
HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Into 8 cm3 of a mixture of dimethylformamide and dimethylsulfoxide (3-1 by volume), 130 mg of pepstatin and 120 mg of the hydrochloride of tertiobutyl diester of glutamic acid are added. Then 180 mg of BOP and 45 mg of triethylamine are added. After 72 hours of stirring, 15 cm3 of distilled water are added. The precipitate is drained and washed with 15 cm3 of ethyl ether. The product is redissolved in 30 cm3 of methanol. The insoluble residue is separated by filtration and the filtrate is evaporated. Then 10 cm3 of a mixture of methylene chloride-trifluoroacetic acid (1:1 by volume) are added, then it is allowed to stand for 30 minutes at a temperature close to 20° C. The mixture is concentrated almost to dryness. Ether is then added. The precipitate formed is separated by filtration and then washed with ether. After drying, 130 mg of pepstatin-glutamic acid are obtained whose characteristics are as follows:

Aufarbeitung

  1. washwashed with 15 cm3 of ethyl ether
  2. dissolutionThe product is redissolved in 30 cm3 of methanol
  3. customThe insoluble residue is separated by filtration
  4. customthe filtrate is evaporated
  5. additionThen 10 cm3 of a mixture of methylene chloride-trifluoroacetic acid (1:1 by volume) are added
  6. waitto stand for 30 minutes at a temperature
  7. customclose to 20° C
  8. concentrationThe mixture is concentrated almost to dryness
  9. additionEther is then added
  10. customThe precipitate formed
  11. customis separated by filtration
  12. washwashed with ether
  13. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-332933489e444da8931f5f60169388c7
Quelldatensatz
uspto-grants-1980_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04185096

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