1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → Di-tert-butyl 2,2'-(3-(5-(benzyloxy)-2-bromophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetate

HRID 1486866Notes

Reaction equation

HRID 1486866 reaction equation
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[CH2:15]([O:22][C:23]1[CH:24]=[CH:25][C:26]([Br:42])=[C:27]([C:29]2[CH2:33][C:32]([CH2:38]C(O)=O)([CH2:34][C:35]([OH:37])=[O:36])[O:31][N:30]=2)[CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:15]([O:22][C:23]1[CH:24]=[CH:25][C:26]([Br:42])=[C:27]([C:29]2[CH2:33][C:32]([CH2:38][C:6]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:5])([CH2:34][C:35]([O:37][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:36])[O:31][N:30]=2)[CH:28]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine3×HCID 1182927882,2'-(3-(5-(Benzyloxy)-2-bromophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetic acid

Product 1

HCID 118292813Di-tert-butyl 2,2'-(3-(5-(benzyloxy)-2-bromophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetateYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,1-Di-tert-butoxy-N,N-dimethylmethanamine (22.11 g) was added dropwise to a mixture of 2,2′-(3-(5-(benzyloxy)-2-bromophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetic acid (9.75 g) and toluene (100 mL) at 100 C, and the obtained mixture was stirred at 100 C for 30 minutes. Further, 1,1-di-tert-butoxy-N,N-dimethylmethanamine (5.53 g) was added thereto, and the obtained mixture was stirred at 100 C for 30 minutes. Further, 1,1-di-tert-butoxy-N,N-dimethylmethanamine (2.211 g) was added thereto, and the obtained mixture was stirred at 100 C for 30 minutes. The reaction mixture was concentrated under reduced pressure, and then, the residue was purified by silica gel column chromatography (ethyl acetate/hexane). The obtained residue was washed with hexane to obtain the title compound (5.73 g).

Workup

  1. stirringthe obtained mixture was stirred at 100 C for 30 minutes
  2. stirringthe obtained mixture was stirred at 100 C for 30 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  5. washThe obtained residue was washed with hexane

Sources & evidence

ORD record
ord-2157aa7a9ef647da84142b6fd76a5ba2
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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