4-Nitrophenol → HCID 131716968, compound

HRID 2248034Notes

Reaction equation

HRID 2248034 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:22]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[CH:29]1[C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=[C:31](O)[CH:30]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:22]([NH:24][CH2:25][C:26]([O:28][C:31]1[CH:30]=[CH:29][C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=1)=[O:27])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 10222114HCID 10222114, compound

Product 1

HCID 131716968HCID 131716968, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.6 g (1.0×10-2 mol) of MA-Gly-Phe-Leu-Gly-OH was esterified with p-nitrophenol (1.1×10-2 mol) in 55 ml of THF by means of dicyclohexylcarbodiimide (DCC) (1.1×10-2 mol). After 3 hours at 15° C. and 12 hours at 25° C., the dicyclohexylurea was filtered off and the remaining solution was evaporated under reduced pressure. The residue was solidified by adding dry ethyl ether and after recrystalisation from acetone:ether (3:1) gave MA-Gly-Phe-Leu-Gly-ONp in 76% yield which was analytically pure; m.p. 124°-8° C. Aminoacid analysis gave Gly:Leu:Phe of 2.0:1.0:0.99.

Workup

  1. filtration12 hours at 25° C., the dicyclohexylurea was filtered off
  2. customthe remaining solution was evaporated under reduced pressure
  3. additionby adding dry ethyl ether
  4. customafter recrystalisation from acetone:ether (3:1)

Sources & evidence

ORD record
ord-b23b876f438146da93e295af5eff3768
Source dataset
uspto-grants-1991_08
Patent number
US05037883

Reaction notes

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