Reaktion #1010611

ord-6c68367cb04841a09710ad447ecfc85c

Reaktionsgleichung

CC(C)(C)OC(=O)[C@H](N)c1ccccc1.Cl
(R)-tert-butyl 2-amino-2-phenylacetate hydrochloride
CCOC(=O)CCCBr
ethyl 4-bromobutanoate
O=C([O-])[O-].[K+].[K+]
K2CO3
→
CCOC(=O)CCCN[C@@H](C(=O)OC(C)(C)C)c1ccccc1
title compound
Ausbeute 74.0%
CCOC(=O)CCCN[C@@H](C(=O)OC(C)(C)C)c1ccccc1
(R)-ethyl 4-(2-tert-butoxy-2-oxo-1-phenylethylamino)butanoate
Ausbeute 74.0%

Edukte

CC(C)(C)OC(=O)[C@H](N)c1ccccc1.Cl
(R)-tert-butyl 2-amino-2-phenylacetate hydrochloride
CCOC(=O)CCCBr
ethyl 4-bromobutanoate
O=C([O-])[O-].[K+].[K+]
K2CO3

Reagenzien

Keine

Lösungsmittel

CC#N
CH3CN
CCOC(C)=O
EtOAc

Reaktionsbedingungen

Temperatur
50°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with H2O and brine
  2. 2
    TrocknenThe organic was then dried (MgSO4)
  3. 3
    Filtrationfiltered
  4. 4
    Einengenconcentrated
  5. 5
    SonstigePurification by chromatography (silica gel, 40% EtOAc in Hexanes)

Vorschrift

A mixture of (R)-tert-butyl 2-amino-2-phenylacetate hydrochloride (0.5 g, 2.051 mmol), ethyl 4-bromobutanoate (0.44 g, 2.26 mmol), and K2CO3 (1.13 g, 8.21 mmol) in CH3CN (10 mL) was heated to 50° C. for 40 hours. The mixture was diluted with EtOAc and then washed with H2O and brine. The organic was then dried (MgSO4), filtered and concentrated. Purification by chromatography (silica gel, 40% EtOAc in Hexanes) afforded 486 mg (74%) of the title compound. MS (ESI) m/z 322 (M+H)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09278922B2uspto-grants-2016_03