4-Nitrophenol → HCID 60073852, compound

HRID 1061691Notes

Reaction equation

HRID 1061691 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:26]([N:29]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:32]([CH2:41][C:42]([NH:44][C@@H:45]([CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:46](O)=[O:47])=[O:43])[C:31](=[O:56])[CH:30]1[CH:57]([CH3:59])[CH3:58])(=[O:28])[CH3:27]>C(OCC)(=O)C>[C:26]([N:29]1[CH:34]=[C:33]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:32]([CH2:41][C:42]([NH:44][C@@H:45]([CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:46]([O:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:47])=[O:43])[C:31](=[O:56])[CH:30]1[CH:57]([CH3:59])[CH3:58])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 60073834HCID 60073834, compound

Product 1

HCID 60073852HCID 60073852, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Nitrophenol (1.39 g) and dicyclohexylcarbodiimide (2.01 g) are added to a solution of (2S)-2-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenylpropionic acid (4.30 g, Compound No. 13-1) in ethyl acetate (100 ml), and the mixture is stirred overnight. The resulting impurity is filtered out, then the filtrate is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled compound (4.52 g).

Workup

  1. filtrationThe resulting impurity is filtered out
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3c6258bd79a424699e501a650d8aabb
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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