Dimethylformamide dimethyl acetal → HCID 178444118, compound

HRID 1464335Notes

Reaction equation

HRID 1464335 reaction equation
[O:1]=[C:2]([CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:15]OC(OC)N(C)C.[NH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:27][CH:26]=1>C1C=CC=CC=1.O1CCCC1>[C:40]([O:39][C:37]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:28]1[CH:29]=[CH:30][C:25]([CH2:24][NH:23][CH:15]=[C:3]([C:2](=[O:1])[CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:26][CH:27]=1)=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 99710734'-(Aminomethyl)-biphenyl-2-carboxylic acid 1,1-dimethylethyl esterHCID 57198439HCID 57198439, compound

Product 1

HCID 178444118HCID 178444118, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-oxo-4-nonenate (1.00 g, 5.04 mmol) and N,N-dimethylformamide dimethyl acetal (0.94 ml, 7.08 mmol) in benzene (10 ml) was stirred at 70° C. for 1.5 hours under nitrogen stream. After cooling, a solution of 4-aminomethyl-2'-t-butoxycarbonylbiphenyl (2.86 g, ca. 10.1 mmol) in tetrahydrofuran (15 ml) was added to the reaction solution and the solution was stirred at room temperature for 2 hours and then concentrated to dryness. The resulting residue was purified by column chromatography on silica gel. The column was eluted with dichloromethane-ethyl acetate (1% to 5%) to give 1.65 g (66.6%) of the title compound as an oil.

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrated to dryness
  3. customThe resulting residue was purified by column chromatography on silica gel
  4. washThe column was eluted with dichloromethane-ethyl acetate (1% to 5%)

Sources & evidence

ORD record
ord-aed3184190724931adca3a6bec1e9707
Source dataset
uspto-grants-1994_04
Patent number
US05304565

Reaction notes

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