Potassium Carbonate → HCID 59540305, compound

HRID 923429Notes

Reaction equation

HRID 923429 reaction equation
Cl.[NH2:2][C@H:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].Br[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C([O-])([O-])=O.[K+].[K+]>CC#N.CCOC(C)=O>[C:7]([O:6][C:4](=[O:5])[C@H:3]([NH:2][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 56777188H-D-Phg-otbu hcl

Product 1

HCID 59540305HCID 59540305, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

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)+.

Workup

  1. washwashed with H2O and brine
  2. dry with materialThe organic was then dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by chromatography (silica gel, 40% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-6c68367cb04841a09710ad447ecfc85c
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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