4-Nitrophenyl chloroformate → HCID 86678417, compound

HRID 882652Notes

Reaction equation

HRID 882652 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].[C:25](Cl)(=[O:36])[O:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1>O1CCCC1>[N+:33]([C:30]1[CH:31]=[CH:32][C:27]([O:26][C:25]([NH:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=[O:36])=[CH:28][CH:29]=1)([O-:35])=[O:34]

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 135021004-Methylbenzene-1-sulfonic acid--benzyl beta-alaninate (1/1)

Product 1

HCID 86678417HCID 86678417, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg (0.57 mmol) of commercially available 4-methylbenzenesulphonic acid-benzyl beta-alaninate and 229 mg (1.14 mmol) of 4-nitrophenyl chlorocarbonate were taken up in 15 ml of tetrahydrofuran and the reaction mixture was then heated to reflux for 30 min. Subsequently, the reaction mixture was concentrated under reduced pressure and the residue was purified by means of preparative HPLC. After concentration of the corresponding fractions and drying of the residue under high vacuum, 86 mg (44% of theory) of the title compound were obtained.

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureto reflux for 30 min
  3. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by means of preparative HPLC
  5. dry with materialAfter concentration of the corresponding fractions and drying of the residue under high vacuum, 86 mg (44% of theory) of the title compound
  6. customwere obtained

Sources & evidence

ORD record
ord-851592ea8bfa43b4a6231cdd99e253c5
Source dataset
uspto-grants-2015_03
Patent number
US08992932B2

Reaction notes

Loading…