Boron trifluoride etherate → Leucine, N-carboxy-, N-benzyl ester, L-

HRID 1009303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009303
[CH3:1][C:2]1([CH2:6][O:7][C:8](=[O:25])[C@@H:9]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:5][O:4][CH2:3]1.B(F)(F)F.CCOCC.C(N(CC)CC)C>C(Cl)Cl>[CH2:18]([O:17][C:15](=[O:16])[NH:14][CH:9]([C:8]12[O:7][CH2:6][C:2]([CH3:3])([CH2:5][O:4]1)[CH2:1][O:25]2)[CH2:10][CH:11]([CH3:12])[CH3:13])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1.[NH:14]([C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[C@H:9]([C:8]([OH:25])=[O:7])[CH2:10][CH:11]([CH3:13])[CH3:12]

Komponenten

6

Edukt 3

HCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 67298758(2S)-2-benzyloxycarbonylamino-4-methyl-pentanoic acid 3-methyloxetan-3-ylmethyl ester

Produkt 2

HCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 67298262[3-Methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-carbamic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(2S)-2-Benzyloxycarbonylamino-4-methyl-pentanoic acid 3-methyloxetan-3-ylmethyl ester (Cbz-Leu oxetane ester) (2 g, 5.7 mmol) was dissolved in dry CH2Cl2 (10 mL) under nitrogen. BF3.Et2O (40 μl, 0.3 mmol, 0.054 eq.) was diluted in dry CH2Cl2 (1 mL) and added to the reaction flask. The reaction was allowed to warm up to room temperature and stirred for 12 h. Triethylamine (335 μl, 3.3 mmol, 0 0.58 eq) was added and the reaction was stirred for an additional 30 min., before being concentrated to thick oil. The crude product was redissolved on EtOAc (15 mL), washed with 3% NH4Cl (10 mL), and saturated NaCl (10 mL), dried (MgSO4), and evaporated to dryness. The reaction yielded a colorless thick oil, which crystallized on standing to give [3-methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-carbamic acid benzyl ester, (Cbz-Leu-OBO ester).

Aufarbeitung

  1. additionadded to the reaction flask
  2. stirringthe reaction was stirred for an additional 30 min.
  3. concentrationbefore being concentrated to thick oil
  4. dissolutionThe crude product was redissolved on EtOAc (15 mL)
  5. washwashed with 3% NH4Cl (10 mL), and saturated NaCl (10 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customThe reaction yielded a colorless thick oil, which
  9. customcrystallized

Quellen und Nachweise

ORD-Eintrag
ord-189b4faf0fc3405c95c9a3a5c8ec8e83
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973037B2

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