Dichloromethane → HCID 14888694, compound

HRID 1647070Notes

Reaction equation

HRID 1647070 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[CH:10]([NH:19][C:20](=[O:22])[CH3:21])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N(C(F)(F)F)S([S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])(=O)=O)C=CC=CC=1.ClCCl.C(N(CC)CC)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9](=[O:23])[CH:10]([NH:19][C:20](=[O:22])[CH3:21])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 14888693HCID 14888693, compoundHCID 131717728HCID 131717728, compound

Product 1

HCID 14888694HCID 14888694, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 8.30 g (0.026 mol) of rac.-2-acetamido-3-[3-hydroxyphenyl)propanoic acid benzyl ester and 10.0 g (0.028 mol) of N-phenyl-N-trifluoromethyl 1,1,1-trifluoromethyl sulfonyl sulfonamide in 110 mL of freshly distilled dichloromethane was cooled in an ice bath and 4.10 mL (0.029 mol) of triethylamine was added dropwise. The resulting mixture was stirred 1 hour at 0° C. and was allowed to warm to room temperature over 2 hours. The mixture was diluted with 250 mL of ethyl acetate and was washed with successive 50 mL portions of water, 1N sodium hydroxide, 1N hydrochloric acid, water, and brine and was dried over magnesium sulfate. Filtration and concentration afforded an oil which was purified by preparative chromatography on a Waters Prep 500 liquid chromatograph fitted with two Prep-Pak silica gel cartridges, eluting with 40% ethyl acetate-hexane to give 10.02 g (85%) of rac.-2-acetamido-3-[3-[(trifluoromethylsulfonyl)oxy]phenyl]propanoic acid benzyl ester.

Workup

  1. temperatureto warm to room temperature over 2 hours
  2. washwas washed with successive 50 mL portions of water, 1N sodium hydroxide, 1N hydrochloric acid, water, and brine
  3. dry with materialwas dried over magnesium sulfate
  4. filtrationFiltration and concentration
  5. customafforded an oil which
  6. customwas purified by preparative chromatography on a Waters Prep 500 liquid chromatograph
  7. customfitted with two Prep-Pak silica gel cartridges
  8. washeluting with 40% ethyl acetate-hexane

Sources & evidence

ORD record
ord-fbf10e91cc164ea29cc9561f6dff134f
Source dataset
uspto-grants-1993_01
Patent number
US05182263

Reaction notes

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