Toluene → HCID 66636739, compound

HRID 1094318Notes

Reaction equation

HRID 1094318 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[O-:21][C:22]#[N:23].[Na+]>>[C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)(=[O:21])[NH2:23]

Participants

4

Reactant 3

HCID 1140TolueneHCID 517096Sodium CyanateHCID 66636944HCID 66636944, compound

Product 1

HCID 66636739HCID 66636739, compoundYield 55%

Procedure

To a solution of methyl (2R)-2-(4-aminophenyl)propanoate (3.0 g, 18.1 mmol) in toluene (50 ml) conc. H2SO4 (0.47 ml, 50 mmol) was slowly added. Then sodium cyanate (1.88 g, 28 mmol) was added to the suspension and the reaction mixture refluxed for 24 h. After cooling at room temperature, the mixture was washed with a saturated aqueous solution of NH4Cl (2×30 ml), dried over anhydrous Na2SO4 and evaporated under vacuum to give a crude that, after purification by flash chromatography (n-hexane/EtOAc 1:1) afforded the methyl (2R)-2-[4-(carbamoylamino)phenyl]propanoate (2.07 g, 9.95 mmol) as white solid (55%). 1H-NMR (CDCl3): δ 9.35 (bs, 1H, CONH), 7.45 (d, 2H, J=7 Hz), 7.25 (d, 2H, J=7 Hz), 6.55 (bs, 2H, CONH2), 3.75 (m, 1H), 1.50 (d, 3H, J=7 Hz).

Workup

  1. temperaturethe reaction mixture refluxed for 24 h
  2. washthe mixture was washed with a saturated aqueous solution of NH4Cl (2×30 ml)
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated under vacuum
  5. customto give a crude that,
  6. customafter purification by flash chromatography (n-hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-fb014ec003f845088ad1c5cadbd2f44b
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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