1,2-Dibromoethane → HCID 69588086, compound

HRID 720198Notes

Reaction equation

HRID 720198 reaction equation
Br[CH2:2][CH2:3]Br.C([O-])([O-])=O.[K+].[K+].[CH3:11][O:12][C:13](=[O:46])[CH:14]([NH:26][C:27](=[O:45])[CH:28]([NH:32][S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[N+:42]([O-:44])=[O:43])(=[O:35])=[O:34])[CH2:29][O:30][CH3:31])[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1.OS([O-])(=O)=O.[K+]>CN(C=O)C>[CH3:11][O:12][C:13](=[O:46])[CH:14]([N:26]1[CH2:3][CH2:2][N:32]([S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[N+:42]([O-:44])=[O:43])(=[O:34])=[O:35])[CH:28]([CH2:29][O:30][CH3:31])[C:27]1=[O:45])[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 516920Potassium bisulfateHCID 695880032-[3-Methoxy-2-(2-nitro-benzenesulfonylamino)-propionylamino]-3-naphthalen-2-yl-propionic acid methyl ester

Product 1

HCID 69588086HCID 69588086, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1,2-Dibromoethane (11 mL, 125 mmol) and K2CO3 (15.5 g, 112.3 mmol) are added to a 2-[3-methoxy-2-(2-nitro-benzenesulfonylamino)-propionylamino]-3-naphthalen-2-yl-propionic acid methyl ester, 59, (6.4 g, 12.4 mmol) solution in anhydrous DMF (30 mL). The reaction mixture is stirred at 60° C. overnight. The reaction mixture is cooled to room temperature and the pH is 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 5.6 g (85% yield) of the desired product. 1H NMR (300 MHz, CDCl3, δ): 7.89 (m, 1H), 7.70 (m, 3H), 7.57 (m, 3H), 7.47 (m, 1H), 7.41 (m, 2H), 7.30 (d, J=8.6 Hz, 1H), 5.39 (m, 1H), 4.37 (s, 3H), 3.62 (m, 4H), 3.46 (m, 2H), 3.35 (m, 1H), 3.20 (m, 2H), 3.13 (s, 3H); 13C NMR, δ 170.4, 165.7, 156.5, 147.9, 134.2, 134.1, 133.6, 133.4, 132.6, 132.4, 130.8, 128.4, 127.8, 127.7, 127.2, 126.4, 126.0, 124.6, 74.1, 65.0, 58.9, 58.1, 52.7, 44.3, 41.8, 34.3.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionThe solution is extracted with EtOAc (3×100 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7849aefff11842da9237aa001d7795a4
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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