Citric Acid → Fmoc-L-aspartyl (t-butyl)-3-(aminomethyl)-benzoic acid

HRID 1682527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1682527
[NH:1]([C:10]([O:12][CH2:13][CH:14]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][C:4](=[O:6])[OH:5].Cl.[NH2:28][CH2:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([OH:35])=[O:34].C(N(C(C)C)CC)(C)C.C(O)(=O)[CH2:49][C:50]([CH2:55]C(O)=O)([C:52](O)=O)O>CN(C=O)C>[C:10]([NH:1][C@H:2]([C:7]([C:38]1[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[C:31]([C:50]([CH3:55])([CH3:52])[CH3:49])[C:30]=1[CH2:29][NH2:28])=[O:9])[CH2:3][C:4](=[O:6])[OH:5])([O:12][CH2:13][CH:14]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11]

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 7019016Fmoc-L-aspartic acidHCID 162187723-(Aminomethyl)benzoic acid hydrochloride

Produkt 1

HCID 131720031Fmoc-L-aspartyl (t-butyl)-3-(aminomethyl)-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of FmocAsp (But) OPfp (17.33 g, 30 mmol) and the compound of Step 6 (6.19 g, 33 mmol) in 50 mL DMF cooled in an ice bath was added 11.5 mL (66 mmol) diisopropylethylamine, and after stirring at room temperature for 5 h, 200 mL 5% citric acid was added and the solution was extracted with ethyl acetate twice. The combined extracts were washed with brine, dried (MgSO4), and concentrated to give a solid which was washed with ether-petroleum ether and dried. Yield 16.3 g (100%).

Aufarbeitung

  1. extractionthe solution was extracted with ethyl acetate twice
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a solid which
  6. washwas washed with ether-petroleum ether
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5fc4301d9d1d458cb627178a525b9f84
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05635477

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