Toluene → tert-butyl N-[(2R)-1-oxo-3-phenylpropan-2-yl]carbamate

HRID 1429405

Reaktionsgleichung

Reaktionsgleichung von HRID 1429405
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.CO>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:10]=[O:11])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 637614Boc-D-phenylalanine methyl esterHCID 9855836Potassium sodium tartarate

Produkt 1

HCID 7020444tert-butyl N-[(2R)-1-oxo-3-phenylpropan-2-yl]carbamateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 21877217Toluene methylene chlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of compound 31c (25.0 g, 90 mmol) in toluene-DCM (4:1, 1000 mL) was added dropwise a solution of DIBAL-H in toluene (1.0 M, 179 mL, 179 mmol) at −78° C. under argon and the mixture was stirred for 1 h at this temperature. Methanol (200 mL) was added immediately to quench the reaction. The reaction mixture was poured into a solution of 200 mL of 20% sodium potassium tartrate (Rochelle salt) and stirred at rt until the two layers separated. The organic layer was concentrated in vacuo and the residue was purified by CC (hexane/EA=2:1) to give compound 31d as a white solid (19.9 g, 89% yield).

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. stirringstirred at rt until the two layers
  4. customseparated
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue was purified by CC (hexane/EA=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-b8132475168d47799b0336f2c18ad427
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940722B2

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