Lithium hydroxide, monohydrate → Boc-D-phe-pro-OH

HRID 726653

Reaktionsgleichung

Reaktionsgleichung von HRID 726653
[NH:1]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@@H:2]([C:10]([N:12]1[CH2:26][CH2:25][CH2:24][C@H:13]1[C:14]([O:16]CC1C=CC=CC=1)=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[OH-].[Li+]>O1CCOCC1.O>[NH:1]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@@H:2]([C:10]([N:12]1[CH2:26][CH2:25][CH2:24][C@H:13]1[C:14]([OH:16])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 11155205Boc-(D)Phe-Pro-OBzl

Produkt 1

HCID 1797945Boc-D-phe-pro-OHAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of Boc-D-Phe-Pro-OBn (145 g, 320 mmol) in p-dioxane (660 mL) was added a solution of lithium hydroxide monohydrate (54 g, 1,280 mmol) in water (330 mL) with vigorous stirring. After 4 hours, the solution was concentrated in vacuo to about one-fourth the original volume and diluted with water (350 mL) and 0.1N sodium hydroxide (100 mL). The aqueous phase was washed three times with diethyl ether (250 mL) and then acidified to pH 3 with solid citric acid which caused a precipitate to form. The solid was filtered, washed twice with water, and then dried under high vacuum, to yield 91 g (78%) of a white solid.

Aufarbeitung

  1. concentrationthe solution was concentrated in vacuo to about one-fourth the original volume
  2. additiondiluted with water (350 mL) and 0.1N sodium hydroxide (100 mL)
  3. washThe aqueous phase was washed three times with diethyl ether (250 mL)
  4. customto form
  5. filtrationThe solid was filtered
  6. washwashed twice with water
  7. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-18f4277f30544b0da926de2bb53bc385
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05710130

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