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

HRID 720199Notes

Reaction equation

HRID 720199 reaction equation
[CH3:1][O:2][C:3](=[O:38])[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][O:35][CH3:36])[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:38])[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][O:35][CH3:36])[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 69588086HCID 69588086, compound

Product 1

HCID 695881352-[3-Methoxymethyl-4-(2-nitro-benzenesulfonyl)-piperazine-1-yl]-3-naphthalen-2-yl-propionic acid methyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-methoxymethyl-4(2-nitro-benzenesulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester, 60, (5.6 g, 10.4 mmol) in anhydrous THF (10 mL) is added 1.0M borane-tetrahydrofuran complex (31.2 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 allowed to stir for twenty minutes. Additional methanol (6 mL) is and the reaction mixture is allowed to warm to the room temperature. The solvent is removed in vacuo and the product purified over silica (EtOAc/Hexane, 1:1) to afford 3.5 g (64% yield) of the desired product. 1H NMR (CDCl3, δ): 8.05 (m, 1H), 7.75 (m,3H), 7.62 (m, 4H), 7.50 (m, 2H), 7.30 (dd, J=8.4, 2.1 Hz, 1H), 3.94 (t, J=6.3 Hz, 1H), 3.66 (s, 3H), 3.58 (t, J=6.8 Hz, 1H), 3.30–2.95 (m, 7H), 2.82 (s, 3H), 2.79 (m, 2H), 2.40 (dt, J=12.7, 4.3 Hz, 1H); 13C NMR, δ 171.8, 148.0, 136.0, 134.1, 133.7, 132.4, 132.0, 131.5, 128.1, 127.9, 127.7, 126.3, 125.8, 124.5, 69.5, 68.7, 58.7, 53.8, 52.8, 51.6, 46.6, 42.8, 35.4.

Workup

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

Sources & evidence

ORD record
ord-c53730555f084c3dab60a029ef06e534
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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