4-Nitrophenol → HCID 131731165, compound

HRID 474176Notes

Reaction equation

HRID 474176 reaction equation
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:4]([NH:6][C@H:7]([C:20]([OH:22])=[O:21])[CH2:8][CH2:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5])[CH3:3].[CH:30]1[C:35]([N+:36]([O-:38])=[O:37])=[CH:34][CH:33]=[C:32](O)[CH:31]=1.C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O>[NH:1]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[C@H:2]([C:4]([NH:6][C@H:7]([C:20]([O:22][C:32]1[CH:31]=[CH:30][C:35]([N+:36]([O-:38])=[O:37])=[CH:34][CH:33]=1)=[O:21])[CH2:8][CH2:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:5])[CH3:3]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 124669052Boc-Ala-Glu(OBzl)-OH

Product 1

HCID 131731165HCID 131731165, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Boc-L-Ala-L-Glu(OBzl)-OH (40.5 g, 0.1 mol) was dissolved in 300 ml of EtOAc and combined with 17 g (0.12 mol) of p-nitrophenol. The reaction was kept at 0° C. for 1 hour. DCC (24.7 g, 0.12 mol) was then added. The reaction was stirred for 1 hour at 0° C. and for 4 hours at room temperature. The precipitate of DCU was filtered off and the solvent was evaporated in vacuum. The residual oil was then dissolved in ether. The precipitate was filtered off and washed with ether and hexane. The yield was 35 g (64%). Rf=0.7 (CHCl3:Et-Ac:MeOH=6:3:1).

Workup

  1. filtrationThe precipitate of DCU was filtered off
  2. customthe solvent was evaporated in vacuum
  3. dissolutionThe residual oil was then dissolved in ether
  4. filtrationThe precipitate was filtered off
  5. washwashed with ether and hexane

Sources & evidence

ORD record
ord-67fbb46a1bef4cfcb6d08b3efc560361
Source dataset
uspto-grants-2014_01
Patent number
US08637521B2

Reaction notes

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