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Hydrochloric Acid → Boc-Pro-Thr(OBzl)-OH

HRID 2107784
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2107784
[N:1]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([O:5]N1C(=O)CCC1=O)=O.N1(C(OC(C)(C)C)=O)[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25](O)=O.[NH2:38][C@H:39]([C:43]([OH:45])=[O:44])[C@@H](C)O.C([O-])(O)=O.[Na+].Cl.O1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1>O>[N:1]1([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([NH:38][C@H:39]([C:43]([OH:45])=[O:44])[C@@H:54]([CH3:53])[O:55][CH2:56][C:57]1[CH:25]=[CH:24][CH:28]=[CH:29][CH:30]=1)=[O:5]
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Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 6288L-ThreonineHCID 312751,4-DioxaneHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 516892Sodium BicarbonateHCID 8538831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) 2-(2,5-dioxo-1-pyrrolidinyl) ester, (2S)-2×

Produkt 1

HCID 14836683Boc-Pro-Thr(OBzl)-OH

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Boc-Pro-Thr(OBzl)-OH was prepared by coupling Boc-Pro-OSu (the N-hydroxysuccinamide ester of Boc-Pro-OH) to H-Thr (OBzl) - OH. H-Thr (OBzl)-OH.HCL was dissolved in 25 ml of water, NaHCO3 (6.21 g, 73.9 mmoles) and a solution of Boc-Pro-Osu (5.07 g, 16.25 mmoles) in 25 ml of dioxane were added. After stirring 3 hours, the reaction mixture was acidified with hydrochloric acid and the product extracted into ethyl acetate. It was washed with 0.2N HCl prepared in saturated aqueous NaCl, saturated NaCl and dried over anhydrous Na2SO4. Solvent was evaporated to yield 6.24 g (mp 120°-12.5°).

Aufarbeitung

  1. extractionthe product extracted into ethyl acetate
  2. washIt was washed with 0.2N HCl
  3. customprepared in saturated aqueous NaCl
  4. dry with materialsaturated NaCl and dried over anhydrous Na2SO4
  5. customSolvent was evaporated
  6. customto yield 6.24 g (mp 120°-12.5°)

Quellen und Nachweise

ORD-Eintrag
ord-a140bd7236e34961af77af8874e44fb7
Quelldatensatz
uspto-grants-1990_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04935493

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