Lithium hydroxide, monohydrate → 3-(Tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoic acid

HRID 1675839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1675839
O[Li].O.[C:4]([O:8][C:9]([NH:11][CH2:12][CH:13]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([F:27])[CH:21]=1)[C:14]([O:16]CC)=[O:15])=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.C1COCC1.CO>[C:4]([O:8][C:9]([NH:11][CH2:12][CH:13]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([F:27])[CH:21]=1)[C:14]([OH:16])=[O:15])=[O:10])([CH3:7])([CH3:5])[CH3:6]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 67338495Ethyl 3-(tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoate

Produkt 1

HCID 673397543-(Tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoic acidAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of Boc2O (1.3 g, 6.1 mmol) and ethyl 3-amino-2-(4-chloro-3-fluorobenzyl)propanoate (1.6 g, 6.1 mmol) in DCM (10 mL) was stirred overnight. The mixture was concentrated in vacuo and chromatographed (SiO2) using DCM as eluent to give ethyl 3-(tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoate. LiOH—H2O (0.26 g, 6.1 mmol) in H2O (7 mL) was added to a solution of ethyl 3-(tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoate (0.55 g, 1.5 mmol) in THF/MeOH (7/7 mL) and stirred overnight. The mixture was concentrated in vacuo, acidifed to a pH of 1 with 1.0N HCl, and extracted with DCM. The DCM extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was chromatographed (SiO2) using 10% MeOH/DCM as eluent to give 3-(tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoic acid (0.5 g). LCMS (APCI+) [M−Boc+H]+ 232.0; Rf: 2.09 min.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with DCM
  3. dry with materialThe DCM extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was chromatographed (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-0ed5578d7ca44345b0cee016db1988c0
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003651B2

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