Sodium Cyanide → 6-(2-Chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoic acid

HRID 2357753Notes

Reaction equation

HRID 2357753 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:5]([C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16])=[CH:4][C:3]=1[S:23]([NH:26][CH2:27][O:28][C:29](=[O:38])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36]C)=[O:35])(=[O:25])=[O:24].[C-]#N.[Na+]>CN(C)P(N(C)C)(N(C)C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:5]([C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16])=[CH:4][C:3]=1[S:23]([NH:26][CH2:27][O:28][C:29](=[O:38])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 68453359Methyl 6-(2-chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoate

Product 1

HCID 684556356-(2-Chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoic acid

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of methyl 6-(2-chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoate (0.060 mole), sodium cyanide (0.060 mole) and hexamethylphosphoramide (Aldrich) (100 mL) is stirred at 75° C. for 24 hours. The volatiles are removed by spin evaporation in vacuo. The residue is dissolved in cold water, and the solution is washed with diethyl ether. The aqueous solution is cooled in an ice bath and acidified by dropwise addition of 1.0 N hydrochloric acid solution (60 mL). The resulting solid may be collected and recrystallized to give 6-(2-chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoic acid. See Greene et al., Protective Groups in Organic Synthesis, Second Edition, (1991) p. 232.

Workup

  1. customThe volatiles are removed by spin evaporation in vacuo
  2. dissolutionThe residue is dissolved in cold water
  3. washthe solution is washed with diethyl ether
  4. temperatureThe aqueous solution is cooled in an ice bath
  5. additionacidified by dropwise addition of 1.0 N hydrochloric acid solution (60 mL)
  6. customThe resulting solid may be collected
  7. customrecrystallized

Sources & evidence

ORD record
ord-846b7100d6f041b9a0fc60569844143d
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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