Dicyclohexylcarbodiimide → 2,5-dioxopyrrolidin-1-yl(S)-3-(3,5-dinitrobenzamido)-3-phenylpropionate

HRID 240230Notes

Reaction equation

HRID 240230 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[C:7]([NH:9][C@H:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][C:12]([OH:14])=[O:13])=[O:8])([O-:3])=[O:2].O[N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[C:7]([NH:9][C@H:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][C:12]([O:14][N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34])=[O:13])=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 44255973(S)-3-(3,5-dinitrobenzamido)-3-phenylpropionic acid

Product 1

HCID 866343152,5-dioxopyrrolidin-1-yl(S)-3-(3,5-dinitrobenzamido)-3-phenylpropionate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

12 g of (S)-3-(3,5-dinitrobenzamido)-3-phenylpropionic acid from reaction b) were dissolved in 120 ml of tetrahydrofuran and admixed with 3.92 g of N-hydroxysuccinimide. With cooling in an icebath at 0-5° C., 7.1 g of dicyclohexylcarbodiimide was added in portions to the reaction mixture. On completion of addition, the mixture was left in the icebath with further stirring until the solution reached room temperature. After the reaction ended (HPLC monitoring >95 area % conversion), the precipitated dicyclohexylurea was filtered off and washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure, and the residue digested at reflux in 250 ml of 2-propanol for 2 h. The product was filtered off with suction, washed with 2-propanol and dried at 50° C. under reduced pressure. The yield was 13.87 g; HPLC purity 98.8 area %.

Workup

  1. additionOn completion of addition
  2. waitthe mixture was left in the icebath
  3. customreached room temperature
  4. filtrationthe precipitated dicyclohexylurea was filtered off
  5. washwashed with tetrahydrofuran
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. temperatureat reflux in 250 ml of 2-propanol for 2 h
  8. filtrationThe product was filtered off with suction
  9. washwashed with 2-propanol
  10. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-cfb75f8d5e244d69bcebab391471214f
Source dataset
uspto-grants-2014_02
Patent number
US08647882B2

Reaction notes

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