4-Nitrophenol → HCID 131716970, compound

HRID 2248039Notes

Reaction equation

HRID 2248039 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:11]([NH:13][C@H:14]([C:16]([OH:18])=[O:17])[CH3:15])=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:5])[CH3:3].[CH:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21](O)[CH:20]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:11]([NH:13][C@H:14]([C:16]([O:18][C:21]1[CH:20]=[CH:19][C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=1)=[O:17])[CH3:15])=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:5])[CH3:3]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 9813836HCID 9813836, compound2×

Product 1

HCID 131716970HCID 131716970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

From 3.6 g of MA-Ala-Val-Ala-OH (0.012 mol), 1.5 g (0.012 mol) of p-nitrophenol, and 2.5 g (0.0125 mol) of dicyclohexylcarbodiimide in 50 ml of tetrahydrofuran was prepared 2.0 g (40% yield) of MA-Ala-Val-Ala ONp; m.p. 174°-6° C. Recrystalized from ethylacetate/hexane. Molar extinction coefficient, ε274 nm =9300 (DMSO).

Workup

  1. customRecrystalized from ethylacetate/hexane

Sources & evidence

ORD record
ord-cf1cfafebe6542dcaedfbe061aeb9b19
Source dataset
uspto-grants-1991_08
Patent number
US05037883

Reaction notes

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