Potassium Carbonate → (S,S)-2-(3-allyl-2-oxo-piperazin-1-yl)-3-naphthalen-2-yl-propionic acid methyl ester

HRID 720162Notes

Reaction equation

HRID 720162 reaction equation
[CH3:1][O:2][C:3](=[O:38])[C@@H:4]([N:16]1[CH2:21][CH2:20][N:19](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[C@@H:18]([CH2:34][CH:35]=[CH2:36])[C:17]1=[O:37])[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.SC1C=CC(O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:38])[C@@H:4]([N:16]1[CH2:21][CH2:20][NH:19][C@@H:18]([CH2:34][CH:35]=[CH2:36])[C:17]1=[O:37])[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 25133905(S,S)-2-[3-Allyl-4-(2-nitro-benzenesulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester

Product 1

HCID 25131150(S,S)-2-(3-allyl-2-oxo-piperazin-1-yl)-3-naphthalen-2-yl-propionic acid methyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S,S)-2-[3-allyl-4-(2-nitro-benzenesulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester, 4, (4.8 g, 8.9 mmol) and 4-mercaptophenol (4.5 g, 35.7 mmol) in DMF (35 mL) is added potassium carbonate (7.4 g, 53.4 mmol). The reaction mixture is stirred 18 hours then quenched with saturated NaHCO3 solution and extracted with EtOAc (200 mL). The extract is dried over Na2SO4 and concentrated in vacuo to afford a bright yellow oil which is purified over silica gel (hexanes/EtOAc, 1:1 to EtOAc/MeOH, 10:1) to afford 2.45 g (79% yield) of the desired product.

Workup

  1. customthen quenched with saturated NaHCO3 solution
  2. extractionextracted with EtOAc (200 mL)
  3. dry with materialThe extract is dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto afford a bright yellow oil which
  6. customis purified over silica gel (hexanes/EtOAc, 1:1 to EtOAc/MeOH, 10:1)

Sources & evidence

ORD record
ord-d7bb79702a3f4033a9fe245fa21d0623
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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