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

HRID 720167Notes

Reaction equation

HRID 720167 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH:4]([N:16]1[CH2:21][CH2:20][N:19](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH:18]([CH2:34][CH:35]2[CH2:37][CH2:36]2)[C:17]1=[O:38])[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+]>CC#N>[CH3:1][O:2][C:3](=[O:39])[CH:4]([N:16]1[CH2:21][CH2:20][NH:19][CH:18]([CH2:34][CH:35]2[CH2:37][CH2:36]2)[C:17]1=[O:38])[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 695880642-[3-Cyclopropylmethyl-4-(2-nitro-benzene-sulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester

Product 1

HCID 695878362-(3-Cyclopropylmethyl-2-oxo-piperazin-1-yl)-3-naphthalen-2-yl-propionic acid methyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-[3-cyclopropylmethyl-4-(2-nitro-benzenesulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester, 13, (3.56 g, 6.46 mmol) and 4-mercaptophenol (4.07 g, 32.3 mmol) in CH3CN (50 mL) is added potassium carbonate (8.91 g, 64.6 mmol). The reaction mixture is stirred for 15 hours, quenched with 10% NaHCO3 solution and extracted several times with EtOAc. The combined extracts are dried over Na2SO4 and concentrated in vacuo to yielding a bright yellow oil which is purified over silica gel (hexanes/EtOAc, 1:1 to EtOAc/MeOH, 10:1) to afford 2.10 g (89% yield) of the desired product. 1H NMR (300 MHz, CD3OD) δ 7.76–7.86 (m, 3H), 7.71 (s, 1H), 7.37–7.52 (m, 3H), 5.27 (dd, J=11.7, 4.8 Hz, 1H), 3.79 (s, 3H), 3.25–3.60 (m, 4H), 2.88–3.06 (m, 2H), 2.62–2.75 (m, 1H), 1.56–1.68 (m, 1H), 1.16–1.29 (m, 1H), 0.01–0.25 (m, 3H), −0.19–−0.08 (m, 2H); 13C NMR (75 MHz, MeOD) δ 171.55, 171.01 m 134.88, 133.78, 132.74, 128.15, 127.52, 127.45, 127.11, 126.11, 125.64, 59.42, 58.92, 51.78, 46.77, 41.23, 36.59, 33.97, 6.63, 3.72, 3.46; MS (ESMS) m/z 367.2 (M+H)+.

Workup

  1. customquenched with 10% NaHCO3 solution
  2. extractionextracted several times with EtOAc
  3. dry with materialThe combined extracts are dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto yielding 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-dc34acf11b9e4068a0559cb3b904d2ae
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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