2-[(6-(2-Chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoyloxymethyl)(1,1-dimethylethyl)amino]-1-(3-chlorophenyl)-1-propanone → 2-[(6-(5-Carboxy-2-chloro-4-[(2-furanylmethyl)amino]phenylsulfonamidomethoxy)(6-oxo)hexanoyloxymethyl)(1,1-dimethylethyl)amino]-1-(3-chlorophenyl)-1-propanone

HRID 2357756Notes

Reaction equation

HRID 2357756 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]CC(Cl)(Cl)Cl)=[O:16])=[CH:4][C:3]=1[S:23]([NH:26][CH2:27][O:28][C:29](=[O:54])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][N:38]([C:50]([CH3:53])([CH3:52])[CH3:51])[CH:39]([CH3:49])[C:40]([C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([Cl:48])[CH:43]=1)=[O:41])=[O:35])(=[O:25])=[O:24]>C(O)(=O)C.[Zn]>[C:15]([C:5]1[C:6]([NH:8][CH2:9][C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[CH:7][C:2]([Cl:1])=[C:3]([S:23]([NH:26][CH2:27][O:28][C:29](=[O:54])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][N:38]([C:50]([CH3:51])([CH3:53])[CH3:52])[CH:39]([CH3:49])[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([Cl:48])[CH:43]=2)=[O:41])=[O:35])(=[O:24])=[O:25])[CH:4]=1)([OH:17])=[O:16]

Participants

4

Reactant 1

HCID 596132162-[(6-(2-Chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoyloxymethyl)(1,1-dimethylethyl)amino]-1-(3-chlorophenyl)-1-propanone

Product 1

HCID 596132152-[(6-(5-Carboxy-2-chloro-4-[(2-furanylmethyl)amino]phenylsulfonamidomethoxy)(6-oxo)hexanoyloxymethyl)(1,1-dimethylethyl)amino]-1-(3-chlorophenyl)-1-propanone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2-[(6-(2-chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoyloxymethyl)(1,1-dimethylethyl)amino]-1-(3-chlorophenyl)-1-propanone (0.060 mole) in acetic acid (100 mL) is cooled in an ice water bath. Zinc dust (0.12 mole) is added in several portions with stirring, and the reaction is stirred for 2.5 hours at 0° C. The mixture is filtered to remove zinc salts, and 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 2-[(6-(5-carboxy-2-chloro-4-[(2-furanylmethyl)amino]phenylsulfonamidomethoxy)(6-oxo)hexanoyloxymethyl)(1,1-dimethylethyl)amino]-1-(3-chlorophenyl)-1-propanone (1220). See Greene et al., Protective Groups in Organic Synthesis, Second Edition, (1991) p. 240.

Workup

  1. stirringthe reaction is stirred for 2.5 hours at 0° C
  2. filtrationThe mixture is filtered
  3. customto remove zinc salts
  4. customthe volatiles are removed by spin evaporation in vacuo
  5. dissolutionThe residue is dissolved in cold water
  6. washthe solution is washed with diethyl ether
  7. temperatureThe aqueous solution is cooled in an ice bath
  8. additionacidified by dropwise addition of 1.0 N hydrochloric acid solution (60 mL)
  9. customThe resulting solid may be collected
  10. customrecrystallized

Sources & evidence

ORD record
ord-3a29539724c640f58dcd27fb2f76e9e0
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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