N-[(phenylmethoxy)carbonyl]-L-tryptophan 1,1-dimethylethyl ester → (S)-tert-Butyl 2-amino-3-(1H-indol-3-yl)propanoate

HRID 2185588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185588
[CH3:1][C:2]([O:5][C:6](=[O:29])[C@H:7]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)[NH:8]C(OCC1C=CC=CC=1)=O)([CH3:4])[CH3:3]>CCO.C(Cl)(Cl)Cl>[CH3:4][C:2]([O:5][C:6](=[O:29])[C@H:7]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)[NH2:8])([CH3:1])[CH3:3]

Komponenten

4

Edukt 1

HCID 15600488N-[(phenylmethoxy)carbonyl]-L-tryptophan 1,1-dimethylethyl ester

Produkt 1

HCID 7020175(S)-tert-Butyl 2-amino-3-(1H-indol-3-yl)propanoateAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of N-[(phenylmethoxy)carbonyl]-L-tryptophan 1,1-dimethylethyl ester (36 g; 98 mmol) in EtOH (150 mL) Pd/C 10% (5 g) was added. A H2 atmosphere was set and hydrogenation was performed with the aid of a Venturi type stirrer. Reaction conversion was estimated by HPLC (Chromatographic method L/46). After 6 h at r.t. the suspension was filtered through paper, then through Millipore® HA 0.45 μm and the filtrate was concentrated under reduced pressure to give a crude oil. The crude was dissolved in CHCl3 (200 mL) and washed with 5% aq. Na2CO3 (200 mL) and brine (150 mL). The organic layer was dried over Na2SO4 and concentrated to give L-tryptophan-1,1-dimethylethyl ester (18.16 g), which was used in the following step without further purification.

Aufarbeitung

  1. customReaction conversion
  2. filtrationAfter 6 h at r.t. the suspension was filtered through paper
  3. concentrationthrough Millipore® HA 0.45 μm and the filtrate was concentrated under reduced pressure
  4. customto give a crude oil
  5. washwashed with 5% aq. Na2CO3 (200 mL) and brine (150 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b455b245edb849018164465498abd2bc
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403055B1

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