Triethylamine → 2-[3-Methoxy-2-(2-nitro-benzenesulfonylamino)-propionylamino]-3-naphthalen-2-yl-propionic acid methyl ester

HRID 720197Notes

Reaction equation

HRID 720197 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]([NH:16][C:17](=[O:23])[CH:18]([NH2:22])[CH2:19][O:20][CH3:21])[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.[N+:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34](Cl)(=[O:36])=[O:35])([O-:27])=[O:26].C(N(CC)CC)C.OS([O-])(=O)=O.[K+]>C1COCC1.O>[CH3:1][O:2][C:3](=[O:24])[CH:4]([NH:16][C:17](=[O:23])[CH:18]([NH:22][S:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[N+:25]([O-:27])=[O:26])(=[O:35])=[O:36])[CH2:19][O:20][CH3:21])[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

7

Reactant 4

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 516920Potassium bisulfateHCID 695877692-(2-Amino-3-methoxy-propionylamino)-3-naphthalen-2-yl-propionic acid methyl ester

Product 1

HCID 695880032-[3-Methoxy-2-(2-nitro-benzenesulfonylamino)-propionylamino]-3-naphthalen-2-yl-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-Amino-3-methoxy-propionylamino)-3-naphthalen-2-yl-propionic acid methyl ester, 58, (4.43 g, 12.1 mmol) and 2-nitrobenzene sulfonyl chloride (2.8 g, 12.7 mmol) are dissolved in any THF (20 mL). The mixture is cooled to 0° C. and triethyl amine (5 mL) is added to the reaction mixture which is then allowed to stir overnight at room temperature. Water (100 mL) is added and the reaction mixture pH adjusted to 3 with 1M KHSO4. The solution is extracted with EtOAc (3×100 mL) and the organic layers are combined and dried over Na2SO4. The solvent is removed in vacuo to afford 6.4 g (quantitative yield) of the desired product. 1H NMR (300 MHz, CDCl3, δ): 8.02 (m, 1H), 7.8 (m, 4H), 7.60 (m, 3H), 7.48 (m, 2H), 7.33 (d, J=8.3 Hz, 1H), 7.20 (d, J=8.3 Hz, 1H), 6.58 (d, J=6.25 Hz, 1H), 4.57 (quartet, J=6.25 Hz, 1H), 4.02 (quartet, J=6.25 Hz, 1H), 3.70 (s, 3H), 3.47 (m, 2H), 3.44 (m, 2H), 3.49 (s, 3H); 13C NMR, δ 171.5, 168.7, 147.9, 134.2, 133.6, 133.5, 133.2, 132.7, 131.0, 128.4, 128.3, 127.9, 127.5, 126.5, 126.1, 125.9, 72.3, 59.1, 56.6, 53.8, 52.7, 38.0.

Workup

  1. extractionThe solution is extracted with EtOAc (3×100 mL)
  2. dry with materialdried over Na2SO4
  3. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-30b9ea2841ee4ac9835a8ad1222e56f4
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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