Diisopropylamine → t-butyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoate

HRID 2392925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2392925
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.C(NC(C)C)(C)C.[C:38]1([CH2:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:18])[CH:44]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:45]([O:47][C:48]([CH3:51])([CH3:49])[CH3:50])=[O:46])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 316203Tert-butyl 2-phenylacetateHCID 36900245-(Carbobenzoxyamino)valeric acid

Produkt 1

HCID 53889532t-butyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoateAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

The target compound was prepared as a colorless solid substance in an amount 5.94 g at a yield of 70.2% in the same manner as in Example 1 except that 5.0 g (19.9 mmol) of 5-(N-benzyloxycarbonylamino)pentanoic acid was dissolved in 50 ml of THF and 3.55 g (21.9 mmol) of CDI was added; 7.83 ml (59.7 mmol) of diisopropylamine and 30 ml of THF were added and 37 ml (59.7 mmol) of 1.63N BA solution was added dropwise; 11.5 g (59.7 mmol) of t-butyl phenylacetate instead of methyl phenylacetate was dissolved in 30 ml of THF; and 50 ml of saturated aqueous ammonium chloride solution was added to the reaction solution, the reaction was terminated, 40 g of 4N hydrochloric acid was added, and 140 ml of ethyl acetate was further added. The analytical results on the target compound are given below.

Aufarbeitung

  1. addition37 ml (59.7 mmol) of 1.63N BA solution was added dropwise
  2. customthe reaction was terminated
  3. addition40 g of 4N hydrochloric acid was added
  4. addition140 ml of ethyl acetate was further added
  5. customThe analytical results on the target compound

Quellen und Nachweise

ORD-Eintrag
ord-00e8081608eb422c94db5d34daf0cf31
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05801271

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