Diisopropylethylamine → (S)-2-tert-Butoxycarbonylamino-3-[(5-chloro-thiophene-2-carbonyl)-amino]-propionic acid

HRID 389639

Reaktionsgleichung

Reaktionsgleichung von HRID 389639
[NH2:1][CH2:2][C@H:3]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:4]([OH:6])=[O:5].CCN(C(C)C)C(C)C.[Cl:24][C:25]1[S:29][C:28]([C:30](Cl)=[O:31])=[CH:27][CH:26]=1>C(Cl)Cl>[C:11]([O:10][C:8]([NH:7][C@@H:3]([CH2:2][NH:1][C:30]([C:28]1[S:29][C:25]([Cl:24])=[CH:26][CH:27]=1)=[O:31])[C:4]([OH:6])=[O:5])=[O:9])([CH3:14])([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 2755946Boc-Dap-OH

Produkt 1

HCID 67155372(S)-2-tert-Butoxycarbonylamino-3-[(5-chloro-thiophene-2-carbonyl)-amino]-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Commercially available (S)-3-Amino-2-tert-butoxycarbonylamino-propionic acid (BOO-Dap-OH) (408 mg, 2 mmol) was suspended in 4 ml DCM and DIPEA (1.75 ml, 10 mmol). 5-Chloro-thiophene-2-carbonyl chloride (362 mg, 2 mmol) (described in WO 2005068456) in 4 ml DCM was added slowly and the mixture was stirred at RT for 2 h. The reaction was filtered and the solvent evaporated. The resulting solid (895 mg) was used without further purification in the next step.

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. customthe solvent evaporated
  3. customThe resulting solid (895 mg) was used without further purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-a0942b99eb52414894521a8ff2412898
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378092B2

Verknüpfte Notizen

Wird geladen…