4-Nitrophenol → HCID 178510998, compound

HRID 2043566Notes

Reaction equation

HRID 2043566 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 Acetate3×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). After stirring at Rt for ca. 5 mins, the reaction mixture became a slurry due to the formation of a gel like precipitate. Stirring was continued at Rt for a further 22 h. The crude reaction mixture was diluted upon the addition of EtOAc (15 ml) then filtered. The filtrate was concentrated under reduced pressure to give an orange/yellow coloured solid. After subjection of the crude material to silica gel flash chromatography (EtOAc), the product PNPO-GlyLys [ε-CBz] [α-Lys] [Boc]2 (Rf 0.4) (344 mg, 66%) was obtained as an off white solid.

Workup

  1. stirringStirring
  2. waitwas continued at Rt for a further 22 h
  3. customThe crude reaction mixture
  4. filtrationthen filtered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give an orange/yellow coloured solid

Sources & evidence

ORD record
ord-eb99af3e52814398be009afd04e33c2b
Source dataset
uspto-grants-2013_11
Patent number
US08586705B2

Reaction notes

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