Cyclopentanol → (S)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid cyclopentyl ester

HRID 2276970

Reaction equation

HRID 2276970 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C@@H:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([OH:17])=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH:28]1(O)[CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH:28]1([O:16][C:15](=[O:17])[C@@H:14]([NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 3

HCID 7298CyclopentanolHCID 24386Thionyl ChlorideHCID 362697(s)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid

Product 1

HCID 57971706(S)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid cyclopentyl esterYield 70%

Conditions

Temperature
70 °C

Procedure

To a solution of stage 1 acid (4.32 g, 12.8 mmol) in cyclopentanol (60 ml) at 0° C. was added slowly thionyl chloride (9.3 ml, 128 mmol). The reaction mixture was stirred and heated under reflux at 70° C. for 2 hours. The excess thionyl chloride was removed by evaporation in vacuo, the reaction mixture was extracted into EtOAc and washed with saturated NaHCO3 solution and dried over Na2SO4, filtered and evaporated to dryness. Flash column chromatography purification with DCM gave the required product (3.6 g, 70% yield). LCMS purity of 100%, (molecular ion not observed).

Workup

  1. temperatureheated
  2. customThe excess thionyl chloride was removed by evaporation in vacuo
  3. extractionthe reaction mixture was extracted into EtOAc
  4. washwashed with saturated NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customFlash column chromatography purification with DCM

Sources & evidence

ORD record
ord-a486a6e8c5624ab3b74c16d1ebf42963
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Linked notes

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