Sodium Cyanate → HCID 69343977, compound

HRID 857120Notes

Reaction equation

HRID 857120 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][C@:6]([CH3:12])([C:8]([O:10][CH3:11])=[O:9])[NH2:7].[O-:16][C:17]#[N:18].[Na+]>C(O)(=O)C.O>[NH2:18][C:17]([NH:7][C@@:6]([CH3:12])([C:8]([O:10][CH3:11])=[O:9])[CH2:5][C:4]1[CH:13]=[CH:14][CH:15]=[C:2]([I:1])[CH:3]=1)=[O:16]

Participants

5

Reactant 2

HCID 517096Sodium CyanateHCID 693445153-Iodo-α-methyl-D-phenylalanine methyl ester

Product 1

HCID 69343977HCID 69343977, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 3-iodo-α-methyl-D-phenylalaninate (0.73 g) in acetic acid (3 ml) and water (1 ml) was treated with sodium cyanate (0.4 g) and stirred for 2 days at 20° C. The solvents were removed under reduced pressure and the residue was diluted with EtOAc. The solution was washed with water, brine, dried (MgSO4) and evaporated to give the title compound (0.82 g) LCMS RT=2.74 min.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionthe residue was diluted with EtOAc
  3. washThe solution was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-a453c96a69eb415f831b87da8b044e50
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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