Potassium Carbonate → tert-butyl N-isopropyl-N-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycinate

HRID 2410589Notes

Reaction equation

HRID 2410589 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=3)[CH2:18][NH:19][CH:20]([CH3:22])[CH3:21])[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32].C([O-])([O-])=O.[K+].[K+].Br[CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>C(#N)C.CCOC(C)=O>[CH:20]([N:19]([CH2:18][C:17]1[CH:23]=[CH:24][CH:25]=[C:15]([C:12]2[N:11]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:32])=[C:4]([CH2:3][O:2][CH3:1])[CH:9]=3)[O:14][N:13]=2)[CH:16]=1)[CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 66678507N-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)propan-2-amine

Product 1

HCID 66677700tert-butyl N-isopropyl-N-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycinateYield 72%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)propan-2-amine (64 mg, 0.15 mmol) was dissolved in ACN (2 mL). K2CO3 (83 mg, 0.60 mmol) and tert-butyl bromoacetate (48 μl, 0.32 mmol) were added and the mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc, washed with water and brine, and then dried over MgSO4. After concentration under vacuum, the crude product was purified by flash chromatography (silica, cHex/EtOAc) to give the title compound as a colorless oil (58 mg, 72%). HPLC (Method A) Rt 5.54 min (Purity: 97.7%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationAfter concentration under vacuum
  4. customthe crude product was purified by flash chromatography (silica, cHex/EtOAc)

Sources & evidence

ORD record
ord-8a30e6d7214543318ad69040d885dbe9
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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