Benzyl chloroformate → Tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-methoxyphenyl)propanoate

HRID 1889153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1889153
[NH2:1][CH:2]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=1)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:20](Cl)(=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:21][C:20]([NH:1][CH:2]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=1)[C:3]([O:5][C:6]([CH3:7])([CH3:9])[CH3:8])=[O:4])=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

4

Edukt 2

HCID 10387Benzyl chloroformateHCID 58545613Tert-butyl 2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate

Produkt 1

HCID 58545693Tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-methoxyphenyl)propanoateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Prepared using General Procedure 2: To a stirred solution of tert-butyl 2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate INT-1 (5.29 g, 19.8 mmol) and TEA (4.29 mL, 29.7 mmol) in DCM (50 mL) at 0° C. was treated with benzyl carbonochloridate (3.00 mL, 21.1 mmol) dropwise over 5 min. After stirring for 10 min, the mixture was washed with 1M HCl (150 mL), dried over MgSO4, and concentrated. The residue was taken up in MeOH (20 mL) and treated with 2 N NaOH (5 mL). After 10 min, the mixture was acidified and the product was purified by chromatography (EA/hexanes) to afford 4.7 g (59%) of tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-methoxyphenyl)propanoate INT-2. LCMS-ESI (m/z) calculated for C22H27NO6: 401; found 424 [M+Na]+, tR=2.47 min (Method 6).

Aufarbeitung

  1. customPrepared
  2. washthe mixture was washed with 1M HCl (150 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. additiontreated with 2 N NaOH (5 mL)
  6. waitAfter 10 min
  7. customthe product was purified by chromatography (EA/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b53e70302ed34f15b6c7730f57a6b52a
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501982B2

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