4-Nitrophenol → HCID 178510998, compound

HRID 2043568Notes

Reaction equation

HRID 2043568 reaction equation
O[NH:2][CH2:3][C:4]([NH:6][C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[O:5].[CH:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18](O)[CH:17]=1.C1CCC(N=C=NC2CCCCC2)CC1.CC[O:43]C(C)=O>>[CH:17]1[C:18]([NH:6][C:7]([C:13]([OH:15])=[O:14])=[O:43])=[CH:19][CH:20]=[C:21]([N+:22]([OH:24])=[O:23])[CH:16]=1.[NH2:2][CH2:3][C:4]([NH:6][C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[O:5]

Participants

5

Reactant 4

HCID 9804-NitrophenolHCID 8857Ethyl Acetate2×HCID 10868DicyclohexylcarbodiimideHCID 131731048HCID 131731048, compound

Product 1

HCID 178510998HCID 178510998, compound

Procedure

To a magnetically stirred solution of HO-GlyLys [ε-CBz] [α-Lys] [Boc]2 (430 mg, 0.65 mmol) and EtOAc (10 ml) was added, in the following order, p-nitrophenol (99 mg, 0.71 mmol) and DCC (147 mg, 0.71 mmol). The reaction and product isolation were carried out according to the method described in Example 19.vi Silica gel flash chromatography (EtOAc) provided PNPO-GlyLys [ε-CBz] [α-Lys] [Boc]2 (Rf 0.4) (344 mg, 66%) as an off white solid.

Workup

  1. customThe reaction and product isolation

Sources & evidence

ORD record
ord-862d3f12a94347e0bdfaa756b47a5304
Source dataset
uspto-grants-2013_11
Patent number
US08586705B2

Reaction notes

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