Sodium Hydroxide → Carbobenzoxy-tyrosyl-glycyl-glycine

HRID 1196814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196814
[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:2]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][C:19]([O:21]C)=[O:20])=[O:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])[C@H:2]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 92643294Z-L-Tyr-Gly-Gly-OMe

Produkt 1

HCID 15024388Carbobenzoxy-tyrosyl-glycyl-glycine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

0.5 g (1.1 mmole) of Z-L-Tyr-Gly-Gly-OMe was dissolved in 3 mL of methanol. Two equivalents of 4 N NaOH were added, and the reaction was stirred for 2 hours, at which time TLC revealed all the starting material had been consumed. (Rf :Z-Tyr-Gly-Gly-OMe, 0.76: Z-Tyr-Gly-Gly-OH, 0.32.) The pH was adjusted to neutrality with 6N HCl and the reaction concentrated under vacuum. 0.5 mL of water was added and the pH dropped to 2. This aqueous solution was washed (4x) with ethyl acetate and the combined ethyl acetate fractions were dried over MgSO4, then concentrated under vacuum. The residue was crystallized from CH2Cl2 /hexanes. Yield 450 mg (95%). M.P. 213°-214° C. (lit. 214°-215° C.). [α]D -23.9 (c 1.2, DMF). Amino acid analysis: tyr1.0, gly1.9.

Aufarbeitung

  1. customhad been consumed
  2. concentrationthe reaction concentrated under vacuum
  3. addition0.5 mL of water was added
  4. additionthe pH dropped to 2
  5. washThis aqueous solution was washed (4x) with ethyl acetate
  6. dry with materialthe combined ethyl acetate fractions were dried over MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was crystallized from CH2Cl2 /hexanes
  9. customM.P. 213°-214° C. (lit. 214°-215° C.)

Quellen und Nachweise

ORD-Eintrag
ord-4b03fcbec7b8478e82dc590b341a15a9
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116741

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