Dimethylformamide → HCID 18678921, compound

HRID 1634699Notes

Reaction equation

HRID 1634699 reaction equation
C(OCC)(=[O:4])C=C.C1(C(N)C2C=CC=CC=2)C=CC=CC=1.[C:22]1([CH:28]([NH:35][CH2:36][CH2:37]C(OCC)=O)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH3:43][O:44][C:45]1[CH:50]=[CH:49][C:48]([S:51](Cl)(=[O:53])=[O:52])=[CH:47][CH:46]=1.C[N:56]([CH:58]=[O:59])C>C(O)C.N1C=CC=CC=1>[OH:4][NH:56][C:58](=[O:59])[CH2:37][CH2:36][N:35]([CH:28]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[S:51]([C:48]1[CH:49]=[CH:50][C:45]([O:44][CH3:43])=[CH:46][CH:47]=1)(=[O:53])=[O:52]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 7036BenzhydrylamineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8821Ethyl AcrylateHCID 18678940HCID 18678940, compound

Product 1

HCID 18678921HCID 18678921, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl acrylate (1.05 g; 10.0 mmol) and diphenylmethyamine (1.83 g; 10.0 mmol) were dissolved in absolute ethanol (25 mL) and stirred overnight at 70° C. The solution was evaporated and crude ethyl 3-(diphenylmethylamino)propionate (2.85 g; 10.0 mmol) was dissolved in DMF (50 mL). 4-Methoxybenzenesulfonyl chloride (2.30 g; 11.0 mmol) and pyridine (10 mL) were added and the mixture stirred overnight at 70° C. The dark reaction was washed with 1 N HCl (2×100 mL). The combined extracts were washed with saturated aqueous NaCl (100 mL), dried over MgSO4, filtered, and evaporated to an oil. The black residue was eluted through a filter pad of silica gel using a hexanes/ethyl acetate step gradient to remove polar material. Preparative HPLC purification, eluting with a mixture of ethyl acetate/hexanes (35:65), gave 1.06 g (23%) of the title compound as a pale yellow oil. 300 MHz 1H-NMR (CDCl3): δ 1.16 (t, 3H), 2.12 (m, 2H), 3.57 (m, 2H), 3.84 (s, 3H), 3.99 (q, 2H), 6.48 (s, 1H), 6.83 (d, 2H), 7.04 (m, 4H), 7.24 (m, 6H), 7.64 (d, 2H).

Workup

  1. customThe solution was evaporated
  2. stirringthe mixture stirred overnight at 70° C
  3. customThe dark reaction
  4. washwas washed with 1 N HCl (2×100 mL)
  5. washThe combined extracts were washed with saturated aqueous NaCl (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to an oil
  9. washThe black residue was eluted through a filter pad of silica gel using a hexanes/ethyl acetate step gradient
  10. customto remove polar material
  11. customPreparative HPLC purification
  12. washeluting with a mixture of ethyl acetate/hexanes (35:65)

Sources & evidence

ORD record
ord-bbd7ca22e7dd4f52955dd5816b9e6b00
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

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