Methanol → 2-[3-Ethyl-4-(2-nitro-benzenesulfonyl)-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester

HRID 720176Notes

Reaction equation

HRID 720176 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH:4]([N:16]1[CH2:21][CH2:20][N:19]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])(=[O:24])=[O:23])[CH:18]([CH2:34][CH3:35])[C:17]1=O)[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.CO>C1COCC1>[CH3:1][O:2][C:3](=[O:37])[CH:4]([N:16]1[CH2:21][CH2:20][N:19]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])(=[O:23])=[O:24])[CH:18]([CH2:34][CH3:35])[CH2:17]1)[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

4

Reactant 2

HCID 887Methanol2×HCID 695877642-[3-Ethyl-4-(2-nitrobenzenesulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester

Product 1

HCID 695877212-[3-Ethyl-4-(2-nitro-benzenesulfonyl)-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-ethyl-4-(2-nitrobenzenesulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester, 32, (5.3 g, 10. mmol) in anhydrous THF (10 mL) is added 1.0 M borane-tetrahydrofuran complex (32.0 mL) at −20° C. The reaction mixture is stirred at this temperature overnight. Methanol (3 mL) is added to the reaction mixture at −20° C. and the solution is allowed to stir for twenty minutes. Additional methanol (6 mL) is added and the reaction mixture is allowed to warm to room temperature. The solvent is removed in vacuo and the product is purified over silica (EtOAc/Hexane: 1:1) to afford 4.1 g (68% yield) of the desired product. 1H NMR (CDCl3, δ): 8.04–7.98m, (1H), 7.80–7.72 (m, 3H), 7.61–7.52 (m, 4H), 7.45–7.38 (m, 2H), 7.28 (d, J=9.6 Hz, 1H), 3.78 (t, J=6.0 Hz, 1H), 3.64 (d, J=11.0 Hz, 1H), 3.50 (s, 3H), 3.48 (t, J=7.2 Hz, 1H), 3.24–3.10 (m, 2H), 3.10–2.95 (m, 1H), 2.90 (t, J=11.0 Hz, 1H), 2.66 (d, J=2.4 Hz), 2.38–2.20 (m, 1H), 1.61–1.48 (m, 1H), 1.48–1.32 (m, 1H), 0.58 (t, J=9.6 Hz, 3H); ); 13C NMR, δ 171.7, 148.0, 135.9, 134.2, 133.7, 132.4, 132.0, 130.9, 128.0, 127.7, 127.6, 126.2, 125.6, 124.4, 69.0, 56.4, 53.8, 51.3, 47.0, 41.9, 35.2, 22.2, 10.7.

Workup

  1. stirringto stir for twenty minutes
  2. customThe solvent is removed in vacuo
  3. customthe product is purified over silica (EtOAc/Hexane: 1:1)

Sources & evidence

ORD record
ord-75b7dbf029d5417d81ceb0908753fa83
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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